


Ten Night Stand

by WannabeLovesPizza



Category: Once Upon a Time (TV)
Genre: Alternate Universe, F/F, Fluff, Fluff Without Much Plot, Game Night, This was supposed to be How to Lose a Swan in 10 Days but I ran out of time, a lot of romcom homages or blatant ripoffs, probably too much hand holding, romcom
Language: English
Status: Completed
Published: 2019-10-13
Updated: 2019-10-13
Packaged: 2020-10-20 08:29:18
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 35,712
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20672339
Author URL: https://archiveofourown.org/users/WannabeLovesPizza/pseuds/WannabeLovesPizza
Summary: Workaholic Regina Mills takes a bet with her sister to have a short fling in return for huge gains at their family company. Non-monogamous serial dater Emma Swan takes a bet from her friend Ruby that she can date the same person for three months. When these two women meet up at the same bar on the same night, all bets are going to get convoluted and messy.





	1. The Match Up

**Author's Note:**

  * For [hollysparrilla](https://archiveofourown.org/users/hollysparrilla/gifts).
  * Inspired by [Ten Night Stand [Art]](https://archiveofourown.org/works/20433410) by [hollysparrilla](https://archiveofourown.org/users/hollysparrilla/pseuds/hollysparrilla). 

> Thank you, thank you **hollysparrilla** for the stellar, fabulous artwork! WOW! Looks like a legit romcom poster! And yes, I totally have it printed and hanging on my wall so I can see it every day. Love it so much. 
> 
> Thanks so very much to **w3llthatdidntwork**! I couldn’t have finished without your cheerleading and support. You’re such a forking talented writer and wonderful friend!:-) 
> 
> Big thanks to **Noname_Kat**! You’re so awesome! Go check out her new fic! (**The Width of a Circle**)
> 
> Thanks so much to the **Elder Swens on Twitter**, y’all rock! Thanks for all the support and head cheerleader Ange!  
Never ending thanks to the **SQUAD**! So glad our leader CS threw us all together :-) Y’all are amazing cheerleaders! Thanks for all the sprints! 
> 
> And huge thanks to SQSN for organizing!

“A hipster bar?” Regina couldn’t help the whine in her voice as she stood outside the bar looking up at the sign that sounded so hipster she rolled her eyes.

Regina Mills had a long, utterly exhausting day at work, and the last thing she wanted to do was meet her sister Zelena for a drink. A drink with her sister usually turned into a long drawn out ordeal at times, especially if Zelena fancied anyone at the bar. Regina wanted to go home, kick off her heels, finish off some emails, curl up with her favorite pasta dish and some wine while falling asleep watching a baking competition show. She took a deep breath and exhaled, feeling the stress of the day coil in her shoulders and neck. She needed to use her meditation phone app more.

The location of their drink had her perplexed, her sister usually preferred the posh places, dare one say snotty places, as Regina walked closer to the entrance she took back her first judgment of the establishment. The bar looked almost downright low key, which immediately charmed her. Regina would never let her sister know she preferred this type of bar than a more upscale one.

As she pushed open the doors, the warm air of the bar hit her, and so did the smell, a mixture of alcohol, sweat, and hipster. Regina scanned the bar and located Zelena sitting at a small table off to the side. Her red-headed sibling raised her glass and smiled.

She loved her sister, yet ever since Zelena had started working for their family company a few years ago, Regina’s blood pressure had gotten higher, and the workload more massive and chaotic. Thankfully, Zelena would go weeks without venturing in the office to wreak havoc, and this drink could go either way. Sometimes Regina wished she could fire her sister, but her parents wouldn’t allow it as silent partners at the firm. A quick drink was an easy fix instead of an all-day weekend gathering with a combo pairing of her sister and parents or some all night sister bonding sleepover.

“Why did you choose this dive bar?” asked Regina as she removed her blazer and swung it on the back of the chair. She looked more casual now in a silk blouse and skirt; the blazer added a fiercer element to the lady boss work ensemble.

“I thought it would be fun,” Zelena smiled brightly at Regina, and then stared hard, “you might even meet someone.” She raised her eyebrows suggestively to Regina.

“Meet someone here?” Regina looked around the packed bar; the crowd ranged from a wide variety of people, none that seemed that upscale for a change. It was a diverse mix, but that wasn’t going to stop Regina from teasing her sister and hopefully shut down any scheme brewing. “For what? Hire a killer? Contract a venereal disease? Learn how to bake cannabis edibles.” She raised her eyebrows in a match to her sister.

“There are a few people here I wouldn’t mind getting a venereal disease from,” Zelena’s eyes scanned the bar, stopping on quite a few of the hunkier men. “Or an enhanced brownie.”

“You’re incorrigible,” Regina snorted, she patted her sister’s arm. “Go get your baby sister a drink.” Regina became engrossed in reading emails on her phone as Zelena gave her an eye roll and trotted over to the bar.

On the other side of the bar at a larger table, a tall brunette with streaks of red in her hair sat with a blonde female couple as they were chatting happily until a taller, slightly older blonde dashed up out of breath and plopped down in a chair.

“Sorry, I’m late,” the blonde pulled off her leather jacket and draped over it over her chair.

The brunette eyed the blonde suspiciously, “Emma, you have that look.” She motioned her hands over Emma’s face.

One of the younger blondes spoke up, “She does! It’s THAT look.” She leaned into the other younger blonde woman and giggled.

“What look?” Emma squinted her eyes at her friends.

“Like you don’t want to face our judgment,” the brunette stared hard at Emma while she took a sip of her drink.

“Argh…” Emma dropped her head to the table “…Ruby…how do you always know?”

“She knows!” yelled one of the younger blondes too loud.

Emma lifted her head, scrunched up her face, and winced at the high pitch screeching of her already drunk friend then dropped her face to the table again. “How is Alice this drunk already?” Emma lifted her head again, reached over, and pulled Alice’s drink away from her. Then she dropped her head back on the table in defeat.

Ruby looked down at her friend’s head on the table and smirked.

“You’ve got like this sheepish walkabout you after you dump someone for a few hours.” Ruby rubbed Emma’s arm then moved to run her fingers through her hair since her head was taking up most of the table. “I know from personal experience.”

Emma groaned loudly from beneath her golden locks splayed across the table.

“Let’s get you a drink,” Ruby stood up and pulled Emma along with her, she continued to push her friend and ex to the bar.

Ruby noticed a stunning redhead by the bar; she maneuvered Emma so they could stand next to her as they waited for their chance to get the bartender’s attention to order more drinks.

Zelena noticed the two attractive women standing next to her; it was hard to miss them as the brunette one dragged the blonde, almost kicking and screaming to the bar. The blonde looked bratty and nearly wild in her tight jeans, knee-high boots, and a white tank top with a black bra visible underneath. A smirk grew wider across Zelena’s face. The two women started talking, so naturally, she leaned in so she could eavesdrop on their conversation.

“So…Lothario Swan, hunting for new prey tonight?” Ruby raised her eyebrows to Emma. “Should I warn all the women about you?”

“Ruby…please…” Emma shifted uncomfortably from one leg to another, “…it was only a one night stand. She knew that going in.”

Ruby let out a long dramatic, sigh yet with sadness in her eyes. “It’s always a one night stand with you, Emma.”

Zelena’s eyes grew wide, still listening to the two women; she pretended to ignore them when the dark-haired woman looked her way. The bartender arrived with her drinks, and she left the bar with a bored look on her face. Oh, she thought, I’m going to have some fun with Regina tonight.

Meanwhile, back at the bar, Emma ran her hands through her hair, waiting for a lecture from Ruby.

“You have let some amazing women slip through your fingers because of your commitment issues,” Ruby stopped and put her hand in front of Emma’s face. “Do not make some finger sex joke right now.”

Emma slumped her shoulders; it was such a perfect set up for a sex finger joke. She furrowed her brows, pursed her lips, and listened to her ex/close friend go on a long monologue on why she should give long term commitment a chance. Emma thought to herself for the same reason she didn’t have a car or house; anything could happen; something terrible could happen at any moment, and it’s going to hurt a whole lot worse if you have deeper attachments.

“Emma, seriously just try dating someone for longer than a week. I promise you it will be worth it,” Ruby tried hard to make eye contact with the male bartender.

“It’s not my thing Rubes…” Emma looked away and then sheepishly brought her eyes to stare at her friend, who yes she did dump a long time ago. “…as you know from personal experience. And before you start, it’s not about monogamy; I could’ve had sex with you for the rest of my life.”

Ruby turned her head so fast to gawk at her ex-lover with fire in her eyes. “Are you fucking kidding me, Swan. You’re the worst.” She slammed her hands down on the bar. Ruby admitted to herself, and it was probably evident on her face, that one stung. She always knew she liked Emma more than Emma liked her, yet they did have a great time together, so it took some time to get over the blonde.

Emma wrapped her arm around Ruby’s shoulder; she waved at the bartender and finally got his attention. She squeezed her hand and rubbed Ruby’s arm.

“Of course, he’s into blondes,” Ruby snapped, she tried unsuccessfully to shove off Emma’s arm. She took a deep breath and bit her lip. “So if it’s not about monogamy or sex, then why don’t you ever date anyone longer than like a hot second?” Ruby had asked this question before, but she felt the need to ask again.

Emma let out a long deep sigh. She didn’t know herself except that her lack of upbringing, moving from foster home to foster home prevented her from putting down roots. And instead of dreaming of one day of having a stable family, she had spent the rest of her life making sure that never happened.

Ruby got a wicked grin on her face as she looked back to Emma, and yes, she thought to herself, maybe she wanted a little revenge from the comment she just heard.

“Swan, you need to grow the fuck up.” She grabbed Emma’s arm from her shoulder; Ruby brought both hands to hold in front of them on the bar. “You’re going to take a bet.”

Emma’s eyes and mouth went wide gaping at her friend. She knew nothing good could come from betting with Ruby. They had a long messy history of betting against each other, then having big fights after and then long, uncomfortable periods of post bet angst. Emma was still sore after losing her beloved car to Ruby, okay, so she did have a car at one time. And she loved that car, and it hurt when she lost that car. She didn’t buy it though; she kind of stole it. However, that didn’t mean Ruby could take it from her.

“Ruby, we agreed for the sake of our friendship and sanity, no…more…bets…ever,” Emma said each word separately for more effect she hoped, and she gave her most serious stare.

Her dark red streaked friend continued to smile big. “I’ll bet you something you want that you can’t date someone for three months.”

Emma rolled her eyes. “I’m not taking that bet. There’s nothing I would want bad enough to date some rando for three months.” She looked at the cocky smirk on Ruby’s face.  
“Yeah, you will,” Ruby licked her lips as her shit-eating grin spread across her face. She knew Emma would cave and take the bet.

The two friends were insanely competitive with each other. One time when they both got step trackers, they walked the entire length of the city before calling a draw and passing out at 4 am with blistered feet and dehydration. One time Ruby’s grandmother Granny asked the two of them to help out in her diner, and the women spent the entire night competing on who could get the most tips. The evening ended in many broken dishes, a black eye, and a broken jukebox that Granny never got an explanation or closure. When Robin and Alice announced they were getting married, Emma and Ruby bet who could throw the best bachelorette party. The party weekend extravaganzas ending up in massive hangovers, a broken nose, and another busted jukebox at Granny’s diner.

“You can’t bet anything that would make it worthwhile to me for that kind of drama,” the bartender finally dropped off their drinks, and Emma took a long swig of her beer.

“Your bug.” Ruby reached over for her glass as Emma was left choking on her recent swallow.

“What?” Emma grabbed a napkin to wipe up her mouth where she had choked, and her beer dribbled down her chin.

“I know you want your beloved bug back after you lost it to me. Here’s your chance,” Ruby smiled as she picked up her drink and walked back to their table.

Emma mumbled to herself, “Yeah, because that bet was completely unfair and stupid,” as she followed Ruby to join their friends.

When Zelena returned to her table, Regina engrossed on her phone didn't look up. She had such a wicked grin as she stared at her workaholic lovelorn sister. She decided to put her devious plan into action; her sister needed to get laid and not tied down by yet another loser — what better way than a cute blonde player woman.

“Regina, when was the last time you had a date?” Zelena appeared casual as her eyes found the commitment-phobe blonde across the room sitting at a table with the dark-haired beauty and two younger blonde women.

“I dated Robin for two years,” Regina said without looking up from her phone. “You know this.” She put down her phone and took a sip of her wine.

“No, that doesn’t count. I mean a date that didn’t lead anywhere,” Zelena’s eyes twinkled.

“What’s the point of that?” Regina squinted her eyes at her sister; Zelena was up to something. She had to make sure to stop drinking; she didn’t want to end up with another random tattoo.

“To have your eyes roll back into your head,” Regina stared at Zelena, utterly confused. “To get laid, dear sister.” She put her hand gently on Regina’s and patted it.

Regina rolled her eyes. “One night stands are not my thing Zelena.” She then tried to put some dramatic weight behind her words by staring intensely into her sister’s eyes. “I’m not a one night stand kind of person.”

“Well…become one. It would be fun for you and dare I say, good for you. Clear out your lady pipes.” Zelena took a long gulp of her frilly fruity drink. “You never dated casually, you always go into these ridiculous long boring engagements. I think you need to date around. Have some one night stands.” Her arm and hand gestures got big and mime like to the point where Regina tried getting her sister to sit back down properly in her chair.

“We have very different definitions of fun and health standards,” Regina sat back down in her chair and smoothed down her hair, which already looked flawless.

“Regina…dear dear sister…” Zelena pouted and puffed her lips out as she stared at Regina.

Regina rolled her eyes. She knew this was about to become pseudo serious, Zelena added an extra ‘dear’ to sister.

“Okay, if not a one night stand…what about a ten night stand?”

“What the hell is a ten night stand?” Regina scrunched up her face to her sister.

“Go out with someone for ten dates, then dump them, or if you get dumped by them before that, then even better!” Zelena had a big grin on her face, and her eyes were sparkling their bright blue color.

Regina stared at her sister, dumbfounded. She didn’t enjoy Zelena’s wacky ideas during meetings and not now either. Her sister’s plans rarely made sense to her or anyone else.

“A fling Regina,” now it was Zelena’s turn to roll her eyes at her sister. “Here, I’ll make it interesting and motivating for you. If you take my bet and win…”

Zelena then held Regina captive by pausing, a long pause as if she was a host on a reality show about to give results and kick someone off. Regina sat still and watched her sister closely.

“I’ll leave the company.”

Regina tilted her head, not that she didn’t love her sister, but working with her at their family company was torture most of the time. Her sister only caused drama and disruption when she was bored enough actually to work in the office, but most importantly, she was terrible at business and got them into horrible and costly situations.

“You can’t be serious,” Regina hoped that Zelena was serious. As Regina studied her sister, she let a loose deep chuckle escape her throat. It was a warm, rich laugh; one people always wanted to hear again and again.

Zelena leaned across the small table and stared intensely into her sister’s eyes. “Can you imagine how smoothly weekly meetings will run without me there? You won’t run out of your precious almond milk in the break room. No more additional harassment training courses because of me.”

The mere idea of Zelena leaving the company or at least becoming a silent partner was immensely appealing to Regina. So much so, she might be willing to take a silly, immature bet from her sister.

“I go on ten dates, and you leave the company? That’s it?” Regina was very skeptical; there was a crazy fine print she couldn’t see yet.

“That’s the bet, dear sister,” Zelena took a sip from her drink. “I pick someone right now for you to go on ten dates. Only ten dates, then it’s over. A fling Regina.”

And there is the crazy hard to read fine print, someone at THIS bar. Regina rolled her eyes and groaned.

“Someone from this place?” Regina looked as if she got hit in the face.

And now her internal debate started in her head to take the crazy bet or make the wise choice and don’t. Oh, she thought, she did want her sister to leave the company. She knew Zelena didn’t enjoy working at the family company, but she didn’t want to push her out either. Zelena was just stubborn enough to stay just to annoy Regina. The internal debate was over; she needed to win this bet and boot her sister out. Kicking Zelena out in a nice way, of course, with a generous severance package and glowing endorsements.

Zelena looked at her with mischievous eyes, “Yes, I’ll pick someone at random from this place, and you go on ten dates with them.” She knew exactly which ‘random’ person she was going to choose. She managed to hold down her smirk.

“Why ten dates?” Regina asked her sister with squinted eyes. She wanted to ask why this place but knew better to provoke her sister further.

“You said no one night stands. And for you, I would imagine this poor soul is only going to get to second base on the sixth or possibly the eighth date, but by maybe by the tenth date, you’ll get a decent shag or some heavy petting…” Zelena took a sip of her drink while she eyed her sister.

Regina pondered this ludicrous idea. “A ten night stand sounds like a plot from an insipid rom-com.”

“Don’t knock silly romcoms; we need them. Especially in the state of the world today,” Zelena pointed up to the tv monitor in the corner of the bar, displaying yet another catastrophe news event.

“Zelena you know I just can’t jump into sex, I need a connection,” Regina stared thoughtfully at her sister. “What if I can’t find that connection in just ten dates?”

“Yes, I forget you’re one of the types I can’t remember… sappysexual? Is that the brainy nerd sex one?” Zelena furrowed her brows as in deep mock concentration.

Regina wanted to smack her sister, okay yes, she wasn’t like most people. She couldn’t just jump into bed with someone. She did need a connection of some sort.

“Zelena, I don’t like labels.”

“Boringsexual? Demineorotic? Is that it?”

Zelena said the last part a little loud; a few nearby tables glanced their way. Regina could feel her cheeks warming.

“At least you’re bi thank gawd. Or are you pan? That would be wonderful.”

Regina lowered her head then decided she wasn’t going to let her sister embarrass her. She hadn’t dated a woman in a long time, not really since her serious relationship in college with Mal. Regina thought they might one day get married, but that didn’t happen. Sometimes it hurt too much to think of dating another woman, so she started dating men again.

Over across the room, another bet was about to take place, with two equally stubborn, competitive women.

“Don’t you want a chance to win back your beloved bug Emma?” Ruby teased her friend.

Emma squinted her eyes at Ruby. She did want her bug back; however, this bet was ludicrous even by Ruby’s standards.

“Ruby, this bet is just stupid. I don’t want to fake date, someone, for three months, that seems mean…” Emma did not like the idea of being forced to date someone, let alone for three months.

“Even for someone like you?”

“Ouch, that hurts Ruby,” Emma stared hard at Ruby. Okay, so she fucked over her friend one time, she did feel bad it didn’t work out between them.

“Fine. Listen, I’ll pick someone out, and you go on one date with them.” Ruby gave Emma a stern look, then put her hand on Emma’s arm and squeezed. “If you like them at all or at least want to fuck their brains out, then you gotta give it a go.”

“Classy,” Emma scoffed at her friend as Ruby let a little laugh escape from her lips.

Their two other friends at the table Robin and Alice watched on in amusement with a little disgust mixed in.

“Maybe the two of you should stop making insane bets with each other,” Robin said delicately in hopes of not setting off her two competitive friends.

Emma and Ruby both glared at Robin.

“Ruby, that bug is mine.” Emma thought she needed to state this fact again.

“Swan, you lost fair and square,” Ruby gave Emma her serious look then raised her eyebrows, “This is your chance to win her back.”

Emma groaned. She already hated this bet.

“This is such a lame bet. I have to date someone for three months?”

“Yes, you have to date the SAME person for three months.”

Emma wanted her yellow bug; she missed that car so much. She thought about the logistics of dating someone for three months. On the upside, work has been so busy Emma probably could only see the person once a week, so that might only be eight dates, as she did the math in her head. Another upside might be having sex for three months; regular sex could be very nice, she thought. She would have to pick the right person, though, for that to work.

“And I pick the person tonight. Here,” Ruby almost cackled to her friend’s shocked face.

“What? Why tonight? Why here?” Emma’s mouth fell open in shock.

Ruby didn’t have a plan, but she thought there were some people at the bar that would make ideal candidates to torture Emma for three long months. She did a once over at the gorgeous redhead standing next to her at the bar. The way the woman ordered a drink seemed obnoxious; the redhead would drive Emma crazy in three hours. Her eyes followed the redhead back to her table and saw her companion, and for some reason, she knew she had to pick the stunning brunette sitting there. For one, she thought, the brunette looked like a tight ass, literally and figuratively, which would drive Emma’s libido and nerves crazy even more than the redhead. Both women looked rich and businessy, which would also work. Since Emma was up and coming at work, she needed someone to match her ambition.

“Because that’s the bet Emma,” Ruby said without a crack in her voice and proud of herself. Ruby admitted to herself, she was going to love seeing her ex and friend tortured a bit throughout this bet.

Emma frantically scanned around the room, looking for any exes or people she knew, this had to be a setup. Why would Ruby pick tonight for this kind of bet? Why did it have to be someone in this bar? Oh please, she thought, don’t be someone from work.

“Do I at least get three passes?” Emma pleaded with Ruby. “C’mon Rubes, that’s only fair.”

Ruby kept a serious face even though she knew Emma would insist on something like this, so she had already picked out three people she knew the blonde would pass on.

“Fine, if you insist.”

Ruby nodded discreetly to a blonde over the in the corner; she knew Emma would find something wrong with the woman.

“Pass, she looks like that barista who always gets my coffee wrong,” Emma scrunched up her face.

Then she motioned to a darker blonde over by the pool table; a few guys were hanging around the woman.

“Pass…hard pass.”

“On what grounds?”

“She’s into dudes,” Emma pointed just as the woman pulled one of the guys by the shirt and started kissing him. “Or at least tonight.”

Damnit, Ruby couldn’t believe her queerdar had been off on that one.

“I get another pass,” Emma shot out with a smug look.

“Fine,” Ruby frantically scanned the room, she needed to land on that smoking hot tight ass brunette last. Thankfully, her eyes fell on a pixie cut dark-haired woman wearing a flower dress with a sweater over it reading a book on birds sitting in a booth. She nodded towards the lone woman for Emma to see.

“Super hard pass. She looks like someone’s mom,” Emma shook her head and took a sip of her drink.

“Okay, but you only have one last pass…let me see…” Ruby pretended to scar the bar once again, then slowly nodded her head to her target table. “Ohhh, there is someone I would approach if not for meeting my true love,” Ruby got a dopey look on her face as she thought of Dorothy. “The redhead over there at one of the small tables.”

Emma looked over slowly across the room to see the redhead sitting at a smaller table. The woman was beautiful, yet there was something about her that spooked Emma. She knew passing on the redhead meant she was Ruby’s mercy for the actual pick. Her eyes slid over to the other woman at the table. Whoa. Emma made her eyes dart away, or they would have stayed there and feasted on the brunette as if she was an all you can eat buffet. Plus, she wanted to seem as disinterested in the brunette as possible in hopes that maybe Ruby would pick her.

“Pass,” Emma turned in her chair to do a slow glance around the bar. “Looks like the bet is a draw, Ruby.”

Ruby fought down a smirk; she knew Emma would be tempted yet ultimately pass.

“Good try, Swan.” Ruby turned her head slowly, scanning the bar too, yet she knew precisely her target for Emma. “So it looks like the woman you’re be dating for three months is…” Ruby paused for dramatic effect and to annoy Emma further, “…the red head’s seatmate…the brunette.”

Emma swallowed hard. She didn’t think Ruby would pick the stunning brunette who seemed to exude elegance and grace despite sitting in a grungy bar eating peanuts and sipping a cold beer. She probably would have hit on the brunette for fun anyway, knowing the woman was out of her league. Emma thought to herself, dating the brunette for three months might not be so bad. And the sex could be phenomenal. However, she needed to reign in her hormones and think practically.

“Uh, that depends if she’s single and remotely interested at all.” Emma pointed her finger at Ruby. “I get another shot if your picks are married or not interested,” Emma subtly looked over to the brunette again, she felt her cheeks warm which was a good or bad sign depending on how she looked at the situation.

“Oh, I won’t need another pick,” Ruby smirked.

Meanwhile, at said table with the intended target and her sister.

“So dear sister, are you ready for your ten night stand?” Zelena wanted to make an addition to the bet; she might as well have fun at the blonde’s cost too. “You can’t date this person longer than ten dates, it must either shrivel and die out before the ten dates end, or you dump their ass.”

Regina scowled at her sister.

“However, I’m sure it won’t take ten dates because any woman will get bored with you on the first date when you don’t put out and just offer a handshake.” Zelena cackle a bit.

“Woman? You never said it had to be a woman?” Regina looked up quickly and met her sister’s eyes with her mouth wide open in surprise.

“Regina, please give men a break, you have the worst taste in men.”

Regina let out a deep, long sigh.

“Fine, date a man AND woman for ten dates.”

“Zelena, please. Work has been insanely busy; I don’t even have time to date at all, let alone two people on some silly bet you have concocted to amuse yourself.” And hopefully, give me some sanity back at work when I win this asinine bet.

“A man would be easier to lose after ten dates.” Zelena oblivious to Regina lost in her thoughts. “All you would have to do is cry after sex, announce on social media every day how much you love him and can’t live without him, or get a plant and animal together.”

“Too many romcoms…” Regina trailed off, eyeing her sister with furrowed brows.

“I’m not sure crying after sex with a woman is going to do the trick, unless you do that ugly crying, you do when you watch that family soap opera you’re addicted to. That crying will scare off anybody.”

Regina furrowed her brows further into a deep scowl. That family soap opera was a well-respected drama, and she did not ugly cry.

“On second thought, I’m not sure that would deter a woman, I think it might mean there was a deep emotional connection,” Zelena was lost in her imaginary relationship thoughts. “Instead, kiss really badly. Talk politics and religion ALL the time, opposite views of hers, of course.”

Zelena started to pretend to randomly glance and search around the bar, picking someone out as her eyes fell on them, just lingering enough to make her sister sweat hopefully. Regina scoffed at everyone she picked. She continued the charade of searching through the bar, squinting her eyes and finding the blonde sitting at a table with a small group of women.

Regina did a sweep of the bar and followed her sister’s eyes. She noticed a beautiful blonde sitting at one of the tables on the other side of the bar. A small chant started in her head, ‘Please, don’t pick the blonde. Please, don’t pick the blonde. Please, don’t pick the blonde.’ She didn’t want Zelena to pick that blonde.

Zelena bit her lower lip; she waited for the right moment to point out the blonde from the bar. “The blonde over there.”

Regina turned her head to take a look at the table Zelena was nodding towards, as discreetly as she could. She saw three blondes and one brunette at the table, so she hoped for a wrongful clarification. “Which blonde? There are three blondes at that table?”

“Regina, darling clearly, the two younger blondes are a couple. The older, more age-appropriate blonde.”

“Sounds like you’re saying I’m old.”

Zelena tilted her head and pursed her lips. “I only speak the truth. Although, seeing you date a millennial would be such delicious fun,” Zelena cackled while Regina rolled her eyes.

“Oh, c’mon Zelena,” Regina felt her stomach drop. She was disappointed in how whiny her voice sounded pleading to her sister.

“What? Since you dated one blonde, you’re never going to date another blonde?”

“You once said you were never dating another Aquarius.”

Zelena rolled her eyes, “I stand by that.”

Regina tried to look over to Emma without getting caught. “Why the blonde?”

“I like the aesthetics,” Zelena smirked to her sister. “My nieces and nephews will be gorgeous.” She winked to Regina. “Go on and talk to her, woo her, dear sister. Weave some kind of magic. You’ll need it to land a date with her.” She lifted her head and nodded towards Emma. “Go get your ten night stand.”

At Emma’s table, Ruby was watching her and holding down a chuckle. Thankfully, their two love bird friends Robin and Alice were too pre-occupied with each other to care about yet another silly bet between their friends.

“Oh, I forgot another part of the bet,” Ruby had a wicked grin on her face.

“Too late, Ruby, no amendments,” Emma stared fiercely at Ruby.

“This one is only going to help you,” Ruby smiled sweetly now, trying to hold back her wolfish grin. “You can’t have sex with her.”

Emma laughed loud and hard. “You can’t be serious? This is no longer a bet; it’s petty revenge.”

“Don’t flatter yourself, Swan. I’m doing you a favor. You always jump too fast into bed, try a different approach this time,” Ruby grabbed Emma’s hand and then said softly as she stared into her friend’s eyes. “I’m trying to help you, Swan.”

“You expect me to date, someone, for three months and not have sex? That’s not possible,” Emma looked way too smug.

“Because you’re so irresistible?” Ruby rolled her eyes. She hated to admit to herself that Emma was right, the blonde could be irresistible at times, and for a short period of time she had fallen for those charms on constant repeat. “Okay…at least wait through a handful of dates or a month.”

Ruby noticed Regina staring at Emma and smiled. “Damn Swan, I think you hooked your target.” This was going to be more fun than she thought if the brunette was already interested in Emma. “She’s the hottest woman in here.”

“What?” Emma asked in between gulps of her beer. Her nerves were getting to her a bit now, was she going to do this? Try and woo some random woman at a bar and hope she can date her for three months to get her yellow baby car back? Yes. Yes, she was. She wanted that car, it was hers, and this was easier than going to Judge Judy to fight her case.

Zelena pushed Regina up from her chair; she then kicked her foot to walk in the direction of the blonde.

At the same time, across the bar, “Emma, make it a little easier on her,” Ruby jabbed Emma in the ribs to get her friend up and to move.

“Geesh, Ruby,” Emma reached for her side in pain. Ruby kicked her foot next. “Fine, okay.” She stood up and started sauntering towards the beautiful brunette headed her way. She hoped she was headed her way, or this was going to be embarrassing. The brunette was stunning and then she noticed a scar on her lip, Emma gulped and felt her palms sweat. She told herself to play it cool, so okay, this might be the most attractive woman you’re ever approached, don’t do anything too silly. Be cool, she told herself again.

As Regina got closer to the blonde swaggering towards her, she felt her cheeks warm, and a trickle of sweat roll down her back. She hadn’t approached a woman in years and certainly not one as eye-catching as this blonde. Her jeans looked painted on; knee high boots looked like something out of a swashbuckler movie and a tank top showing her sculpted arms. Regina had never dated anyone like this woman, getting Zelena stuck in her head all she could think about was having sex with this almost female-like Errol Flynn, all the woman needed was a vest and sword. She had to reign in her libido; she shook her head, trying to calm herself. Damn Zelena.

Luckily, space opened up next to a wall in the bustling bar, thankfully in the middle of both tables. The two women came up to each other and stopped. They stared at each other, willing the other to go first. Then they both spoke at the same time.

“Hey.”

“Hello.”

It was extremely awkward for both women. So they decided to try again at the same time, once again delivering the same greeting to their combined annoyance.

“Hi.” “Hi.”

A duplicate greeting on top of each other again felt even more awkward the second time, if that was possible.

Emma felt a trickle of sweat roll down her back. Get it together Swan, do you want to stick it to Ruby and get your car back? Swan up and get in wooing mode, she told herself.

Regina thought this was one of the worst introductions. What does this blonde woman do for work? She’s certainly not working with clients or greeting people.

“Regina,” she decided to stop the insane cycle, but she couldn’t figure out if a handshake was proper. It seemed a bit odd in terms of possible dating; this wasn’t a business transaction, so she nodded to the blonde instead. Although, perhaps thinking of this as a business transaction would be best to achieve her goal of short term dating and booting her sister from the company.

“Emma Swan,” Emma nodded to Regina and smiled.

“Ridiculous,” the word slipped from Regina’s mouth without precaution. The woman’s name even sounded like a swashbuckler Regina thought.

“Uh, thanks,” Emma replied with a snarky tone as she ran her hand behind her neck. This brunette had thrown her off her game already. Most people thought her name was cute.

“I meant your name,” Regina gritted her teeth, what kind of name was Swan? Utterly ridiculous, she thought, a silly daredevil swashbuckler.

“Yeah, I got that. What’s your last name? Poshington or Smithsonian?” This woman might not be an ideal candidate to date for three months. She was already too high maintenance for Emma’s tastes. Damn Ruby.

“No, it’s Mills,” Regina said proudly as a peacock puffing out all their feathers. “Mills is a classic name with a tapestry of history.”

Tapestry? Who uses a word like that in a sentence like that Emma wondered. “It also means…grinding. Are you a grinder?” Emma tilted her head and smirked. As annoying as the uppity woman was, Emma’s mind couldn’t help but wander below her waist and grinding of a different kind. The woman was attractive, but the air of superiority around her was unattractive.

Regina wanted to knock the smug smirk off the blonde’s face. This woman was distasteful from the red pleather jacket she could see slung over her chair back at her table to the scuffed worn boots she was wearing and the tight jeans she had painted. Regina was furious with her sister for saddling her with this tacky choice. She knew her sister must have known this blonde somehow and picked her on purpose to win this insane wager.

“The Swan family name means just a bird I’m assuming. A bird that carries a variety of diseases.” Regina narrowed her eyes at the blonde.

Emma decided if she would have some fun with the uppity woman. “Mills and Swan…has a nice ring to it. It sounds like we should start a detective agency.” Emma leaned in a bit, putting her arm against the wall to stare more closely at this Regina. “You look like you could pass for a film noir femme fatale.”

“I don’t think that would be a very successful endeavor. I would imagine you would eat a lot of donuts while I did all the leg work,” Regina was thankful she brought over her drink so she could take a sip while she eyed this Emma. “Plus, I don’t think you have the…style for it…pleather is a tad classless.”

Emma thought to herself, while the woman was astute, she did love donuts and pleather; and would love to see this woman’s legs work. Emma realized that she probably did not want to date this woman for three long months. This Regina Mills woman already seemed kind of rude and hard to talk to. She had to get Ruby to pick someone else. Having to endure a three-month charade with this arrogant woman would be an extreme gauntlet she didn’t think she could finish, she thought of her hero Xena and how even the warrior princess would fail this one.

“Some people would say classless is fun and classic is stuffy,” Emma crossed her arms against her chest.

“Yes, those are the same people who eat with their mouths open,” Regina glared at Emma.

Regina also realized, ten dates with this woman would be pretty tedious even despite the wavy long curls her hands wanted to run their fingers through while spooning. Damn her body for betraying her. She knew she wouldn’t be able to convince Zelena to pick someone else. She had to leave this bar either with this woman or firm plans to meet for a first date.

Emma had no idea what else to say to this woman; her brain just turned off in a way it hadn’t before. Her body did not; it was as if her body knew something her brain wasn’t aware of, and that worried her. She decided right then, she would force Ruby to pick someone else, and Emma was reasonably confident she could convince her. And if not, she could steal her car back or come up with another embarrassing bet that Ruby couldn’t refuse. It was decided in her mind, even though it was a brief meeting, she was calling quits on this snotty brunette.

“Well, I’ve got some donuts and pleather…” Emma trailed off, not knowing where her comeback was going, so she decided to cut it short, “…enjoy your evening…uhhh interesting meeting you.” Emma gave one last look over to this Regina; the woman was breathtaking; she begrudgingly admitted as she turned to leave.

Regina’s mind started to race; she couldn’t lose this bet; she desperately wanted Zelena gone from the company, and if this was the only way, so be it. Either she could turn on the charm, although Emma felt like she already tried that or be honest with this woman and see if she could strike up a deal without letting Zelena find out. She reached out and took hold of the blonde’s arm, her fingers brushing Emma’s soft skin and firm bicep. Emma turned around, surprised to see Regina holding onto her arm.

Brown eyes stared into green eyes. Regina took a deep breath, glanced down at her favorite heels, and decided to see where honestly would get her. It was not her best tactic in business, then yet sometimes it did work to varying degrees.

“Wait…” she brought up her eyes again to stare into Emma’s wide eyes, “…my sister bet me…” Regina found it hard to say out loud because it made her sound weak and unattractive, yet she forged on despite her eyes dropping to her shoes again, “…that I couldn’t get a date tonight.” Regina raised her eyes to stare back at Emma; she held her breath, waiting for a response.

Whoa. Emma was extremely surprised, another bet. What are the odds tonight of all nights, and in this bar, Emma wondered. What rom-com hell is this? Or luck? This Regina woman took bets? This fancy-ass snooty woman engaged in juvenile wagers? Despite Regina being hard to talk to and uppity, how could the woman have trouble getting dates? Emma realized she had to stop asking herself so many questions. She wondered if she should tell Regina of her bet. Then she thought about what she would do in a business deal; she would not divulge information that vital while closing a deal.

“You gotta get a date tonight with someone here to win a bet?” Emma narrowed her eyes and stared intensely at Regina.

“Yes, …actually ten dates,” Regina bit her lower lip.

Emma was a little transfixed by Regina biting her lower lip, okay that did something to her insides despite first impressions. “Ten dates with ten people?” What kind of crazy bet was this? “What number am I?”

“No, ten dates with one person. My sister is a bit mad at times,” Regina ran her fingers through her hair, she could tell Emma was watching her confused; the blonde had a dopey look on her face. Then thankfully, the confusion turned possibly into intrigue so that she might win Zelena’s bet after all.

“So you want ten dates with…me?” Emma’s eyebrows shot up in surprise. Oh, I could use this to win Ruby’s bet, after all, she thought. She realized she could stretch ten dates to three months easy.

“Yes, it can be a formal agreement between us. It would just be a show for my egomaniac sister…as long as she never knows…that you know…or we know together.” Regina shook her head; she sounded like a bubbling idiot. Or plot thread from Friends.

“Ah, the old fake dating…” Emma gave Regina a wink. “You didn’t strike me a rom-com nerd.”

Regina scoffed at the blonde’s crazy wink. “Fake dating? This is not some idiotic rom-com trope,” now she was wondering if this blonde was in cohorts with her sister. She took a deep breath. “No. Okay…this is real dating…” She realized her voice wavered, and it almost went up as if asking a question, she wondered, was this fake dating? She wouldn’t have picked this woman to date at all; she was Zelena’s choice or punishment.

“Okay…” Emma leaned in closer, putting on her most charming smile. “You’re asking me out on ten dates? Ten real not fake dates?” This still didn’t feel like a real offer, Emma thought.

Regina knew she was going to regret this; she took a deep breath, hoping to calm her nerves and the desire to murder her sister. “Yes. Dating…what all that entails…activities…outings…sex…” Regina said ‘sex’ quieter than the other parts, and she hated she felt her face grow warm. She was not thinking of having sex right now with this beautiful yet irritating blonde in front of her.

Emma stood momentarily, stunned for a moment. She had never been asked out in quite this way before. Sex. Huh, she usually would jump on the sex part, but she had played down that part because of Ruby’s stupid, cruel addition to the bet. She didn’t know how to respond to this proposal, despite that it could help her immensely.

Regina waited for this Emma to respond. She got nervous with the prolonged silence; she should not have mentioned sex. She paused for a moment; maybe fake dating was better than real dating if this insane person was up for it. “…I thought we could date...without an agenda.”

“Doesn’t all dating have an agenda?” Emma lifted her eyes to start at Regina, asking the question.

Regina squirmed a little; she could always feel when she was about to close a deal. She had no idea right now if she was close or not with this, Emma.

“You must want something pretty bad to win,” Emma smiled at Regina; she knew the feeling. Did this woman also want her beloved car back? What did this woman want to win over her sister?

“I do. And my older sister usually gets her way, so it would be nice to beat her for once,” it was the first sort of sincere thing Regina had said since she started talking to this Emma.

“This could work,” Emma started thinking, this could work to get her yellow baby car back. This woman wanted to win her bet just as much if they joined forces they could both win.

“What could work?” Regina furrowed her brows and looked at Emma for an answer to what seemed like a riddle.

“Nothing, let’s get out some basic info out of the way…are you attached?” Emma leaned in more interested now, invading Regina’s personal space. She noticed the brunette smelled too good; she inhaled again to get another hit.

“Unattached,” Regina shot back to Emma, “You?”

“Single. Are you psycho?” Emma tilted her head and raised her eyebrows.

Regina scoffed. “I’m passionate…if there is a good cause.”

Emma thought that probably translated to possibly unhinged if something went amiss or didn’t go the uppity woman’s way, dully noted that could cause problems after the three months when she needed to dump the woman.

“Where are you on the…sexual spectrum? I’m assuming since you’re asking me out on ten dates, you’re at least bi.” Emma’s eyes glanced down to Regina’s lips then back up to her eyes.

Regina rolled her eyes and grumbled, “I’m not asking you out on ten dates.” Since she had caught this blonde staring at her lips she decided to stare at Emma's mouth; she licked her lips.

Emma raised her eyebrows; she stood so close to Regina; their bodies were nearly flush up against each other. She wanted to move closer, Regina smelled utterly enticing.

“Then, what are you doing? It sounded like you wanted me to go on ten dates with you.” She could have some fun with this uppity woman and get her car back; this might not be such a bad three months.

Regina realized they were standing so close together she could feel the heat coming off Emma’s body. She decided to take her chance on a hutch. “No one is forcing you to go on ten dates with me. Take it or leave it.” She turned to walk away from Emma, this time, it was her turn to make a fake exit.

And this time it was Emma’s hand reaching out and wrapping around Regina’s wrist. She couldn’t let this woman get away; this was a great match for getting her car back and winning over Ruby. “Alright, deal, lady. Ten dates.” Emma dropped Regina’s wrist when she realized her thumb was unconsciously rubbing the smooth, warm skin.

“Meet me by the door,” Regina turned abruptly and headed back to her table with a smirk on her face. She was happy being able to flee the bar and her sister while it was still relatively early, she could get some work done at home.

Zelena looked surprised as Regina strolled over and picked up her jacket, phone, and purse. “Where are you going?”

“I’ve accomplished the start of your bet, I’m going on a date with that blonde woman you picked out,” Regina smoothed down her shirt, ran her head through her hair and took one last sip of her neglected drink.

Zelena had a wicked grin on her face, “Dear sister, if you truly have a one-night stand tonight, I’ll leave the company immediately and pay back all the harassment lawyers.”

Regina knew that lying wasn’t the way to win this bet. “She’s just escorting me home; we have a date next week.”

“There is the Regina that I know and sometimes tolerate,” Zelena beamed up at Regina. “Have a good evening, dear sis, and if the urge hits…just jump her bones and make her moan.” She winked and raised her glass as Regina turned and headed towards the door.

Over across the bar, Emma hurried over and grabbed Ruby’s new beer and drank most of it. She heard a growl as she grabbed her jacket and smiled at her friends.

Ruby gave Emma a side-eye, “Just remember Swan, you can land her tonight, but you gotta keep landing her for three loooooong months.”

“You might as well hand over the keys now, Ruby,” Emma gave a smug grin to Ruby then pointed to Robin at the table. “Robin, you’re the only sober one, make sure they both get home okay.”

“Text me later, Swanova,” Ruby giggled at her own silly name.

Emma turned quickly to glare at Ruby with her hair bouncing on her shoulders. She turned back around to almost collide with Regina by the door. They both took in a deep breath.  
“Are you ready to leave…Ms…Swan?” Regina noticed how ridiculous the name sounded on her tongue, yet also somehow not out of place with regards to the blonde.

“We’re starting our first date now?” Emma’s eyes widened as she followed Regina out of the bar’s main entrance.

When they were safely outside, and of our earshot of one crafty, wicked sister, Regina said softly to Emma, “No, let’s meet next week for date one.”

As she finished her sentence, a car service pulled up, and Regina opened the door for Emma to enter the vehicle, “I’ll drop you off.”

“Uh, thanks,” Emma looked confused as she climbed into the car. She scooted over across the seat to make room for Regina. Emma pulled up on her coat as Regina got into the car and sat beside her. They bumped into each other as they put on their seat belts.

As soon as the car was moving, Regina studied her phone, and Emma sat there a little awkwardly. The first date next week, this was great news. Emma hoped she could string out these ten dates to three months.

“So when do you want to go out?” Emma watched Regina engrossed in her phone, the woman was stunning, and she felt her body react to her. Her traitorous body had been responding to Regina since she first laid eyes on her.

“What’s your email address? Might as well get your phone number…” Regina looked up and stared at Emma, “…but don’t text me all the time and certainly not silly things like a cat knocking something over or a baby burping. Or political stuff.”

Emma rolled her eyes; she wondered how this woman made hysterical memes sound unappealing. “Got it, text all hours of the night with lewd content only.” She stared at Regina, who returned a cold glare. “Here, give me your phone,” Emma reached out to take Regina’s phone, their fingers brushed against each other before the brunette finally relinquished her device. “Don’t worry; you’re getting it back unscathed.”

Regina watched while Emma put in her information into her phone. She bristled at the way the blonde just took her phone. Nobody took her phone; her phone was essential and very private. She could be getting sensitive emails, texts, or calls any minute from work. Regina felt her breathing getting shallow and her pulse quicken, she needed her phone back. She also realized she might be too attached to her phone; she needed to browse the meditation app for a lesson on letting go of your phone for five minutes.

“I have a huge project going on at work…” Regina picked at nails while Emma furrowed her brows and quickly typed in her information into the device, “…and I need my phone back…I don’t have time for dating…but my sister is the most odious woman in the world and…” she knew she had to stop her mouth from nervous talking. She looked up to see Emma staring at her and giving her phone back with a smirk. “Thank you,” Regina replied quietly.

The car pulled up to a stop, Emma reached over and patted Regina’s thigh. She gritted her teeth for reaching out and touching her, stupid hand betraying her.

“Thanks for the ride…I’ll see you next week, right?” Emma felt her cheeks warm; she didn’t mean to sound kind of clingy or unsure. She shook her head, that wasn’t her style. Something was unnerving about this Regina woman. Regina rambled in the car, too; it seemed the anxiety of their situation caught up to both of them. She almost feared what the first date would feel like or if they would make it through.

“Yes, I’ll email you soon,” Regina nodded to Emma. She reached out to shake her hand, then retreated, thinking of her sister’s snide comment.

“I’ll text you back,” Emma smirked to Regina.

Emma took that as her cue to shut the car door. She stood and watched the car disappear down the street. She didn’t know if she could date that woman for three long months, but she smelled good enough to try.

As Regina sat back in her seat, she looked at her phone. It appeared while Emma had her phone that she texted herself a gif of two cats ringing bells for treats. Going on ten dates with that woman was going to be trying, at least the woman was attractive and appeared to like animals.


	2. Date 1

After going back and forth for days on end about when the first date would take place and what they were going to do, the two women finally decided to take turns picking out dates and activities. Regina conceded even though she asked Emma out on ten dates, it would seem a bit unbalanced if she picked out all the dates, so they were cut in half. Regina stated though if Emma picked something truly horrendous, then her date picking privileges were revoked.

Then the debating continued on who would choose first. The emails and texts piled up over the days, and yet no firm date had been set. It turned into a tennis match with ideas and suggestions bouncing and pinging between the two. Every time Regina suggested something Emma didn’t want to do, the blonde would send a poop and crying emoji. Regina was ready to set the blonde’s hair on fire for frustration and crudeness. Emma also loved gifs, and the brunette scowled every time the animated nonsense popped up on her phone; except for the dog and cat ones, those were cute. 

Regina needed to see the new opera for work and thought it would be nice not to go alone for a change, so she suggested to Emma that would be their first date. Well, Regina mostly told Emma that would be their first date and that the blonde could pick the next date activity. And Emma would get a pass, Regina would go along with anything in reason, even if it were terrible Emma’s date picking privileges would stay intake since the blonde so opposed to the opera.

Since this was a short fling, Regina didn’t care what they did just as long as it appeared they were dating, she had to remember to take photos and post them; even though she wasn’t into social media, she knew Zelena was and would be watching. She realized on their drive home that night from the bar that she wouldn’t be opposed to having sex with the blonde, she thought that could be an excellent activity for a date. Regina had hit a dry spell, and her sister always knew when she had sex for some reason, it was a bit maddening, it was like having a superpower. And if she fully admitted to herself, she was in the most irritating way completely attracted to Emma, she wasn’t usually her type, but there was something disarmingly charming about the blonde. And most of the time in an irritating hot way.

Yet she wanted to get to know this Emma better before jumping into bed with her. And she wasn’t sure if the blonde was truly interested in her. She had kind of admitted where she was on the sexual spectrum, but Emma had not that night; in fact, there was a lot about the blonde she didn’t know. Regina had a feeling that Emma could be so inclined to the agreement, including sex. The blonde had stood very close to her and tended to stare too much at her lips.

As the opera date drew closer, Emma sent more dead face emojis along with sobbing ones.

Regina texted back, “Please, dress appropriately Ms. Swan. This is the opera. The opera is high class. Do not show up in jeans or pleather.”

“Overalls got it.” Emma had texted back.

The day before the opera, Regina got another text from Emma. It was a photo of the blonde in actual overalls with a caption, ‘This good?’ Regina wanted to call Emma and chastise her; however, she stared at the photo far too long. Beneath Emma’s overalls, there was only a sports bra. Emma’s finely sculpted bare arms were on display, her long blonde hair was on top of her head in a messy bun, and she was wearing big chunky glasses.

Regina saved the photo to her phone’s camera roll.

She told herself she might need the photo later if Emma turned out to be a psycho, and she went missing on one of their ten dates. Yes, she thought that was the only sole reason she was keeping that photo. It had nothing to do with the fact that the photo quickened her heart rate and sent warm waves of electricity through her body.

Emma had to admit it was fun spamming Regina with texts and emails and watching the stuffy woman’s responses. She didn’t know anything about the woman; they didn’t even exchange what they both did for a living, which was kind of refreshing, she thought. She was very surprised after she sent a photo of herself in overalls as an opera clothing option that Regina sent back a gif. An actual gif. And not so some random gif, it was the classic Blanche Devereaux spraying herself with a water bottle to cool down gif. Emma had sat there stunned for a few minutes, wondering if Regina did like the overalls? Or maybe it was the sports bra? And they turned her on? Or was she playing with her?

Then, even more shocking a few minutes later, Emma received a photo of Regina in a black and white bikini, sticking her tongue out. Emma nearly fell out of her chair at work.

Emma saved the photo to her phone’s camera roll.

When Regina got out of her meeting that, unfortunately, Zelena had shown up for, she noticed her phone was missing. She knew her scheming sister must have taken her device while she was addressing the board members. Regina stormed into Zelena’s office, where her sister had her feet up on her desk with a wicked grin.

“Looking for this?” Zelena waved Regina’s phone over her head in the air.

“Zelena, that is private property,” Regina yelled at her sister as she stomped over to snatch her phone from her sister’s hand gruffly.

“No, it’s your pacifier,” Zelena smirked while she watched Regina frantically go through her texts and emails.

Regina went to her text messages. Oh no, she saw that Zelena had sent a photo to Emma. A bikini photo, great just great, she thought. It was a photo Zelena had taken when they had spent a weekend at their parent’s beach house. And she sent Emma a gif implying that she was turned on by her ridiculous overalls outfit. She was not going to admit to her sister that the overalls photo had some merit, and she certainly wouldn’t have texted that to Emma. She barely knew Emma, they’ve only met one time. Although they had been talking electronically every day for a week, she still didn’t know the woman well enough to send a Golden Girls gif. And definitely not well enough to send a scantily clad photo. Her cheeks burned.

“You texted Emma a photo of me…in that bikini?” Regina couldn’t stop her jaw from opening wide and her eyes as she stared at her sister.

“Emma? So that’s the blonde,” Zelena gave a wicked smile as if she had wicked thoughts racing through her mind. “Yes, you needed to up your flirting game if you’re going to bang her soon.”

“Zelena how many times do I have to tell you NOT to steal my phone,” Regina fumed at her sister, it was one thing to steal her clothes but stealing her phone made her want to throw fireballs at Zelena.

A few co-workers were walking by Zelena’s office then walked faster to get out of the firing zone of the tow notorious fighting sisters.

Regina stormed out of Zelena’s office. She could hear Zelena yell to her, “The overalls were super hot sis. Get it!”

When Regina got back to her office and calmed down a bit, she sent off a text to Emma explaining what happened. The blonde was not surprised to hear that Regina did not send the last few texts, and she specifically thought the emails sending excerpts from lesbian erotica were out of character as well. Although, Emma texted back to tell Regina she was open to her, sending her more porn anytime. Regina nearly dropped her phone, reading the last part.

After apologizing for her sister’s antics, Regina gave out directions on what time and where to meet tomorrow night for the opera. Regina hoped the last few texts hadn’t made things even more awkward between her and Emma. She took a deep breath; it was just a date, no big deal. It had been a long time since she been on an actual date, or had she ever really been on a date? Her previous engagements didn’t seem like dating, and Mal just happened, and quickly they were living together. Regina got more nervous and opened the meditation app this time and pressed start for a two-minute lesson on deep breathing.

Emma couldn’t help the smile from all the texts and emails from Regina today and the previous messages and emails from Regina’s sister, she needed to thank the sister one day. Emma felt she was still drooling over the bikini photo. This dating Regina for three months was going to be fun. She wasn’t super jazzed about going to the opera, she had never been to an opera, and she had absolutely no idea what to wear. Emma had enlisted the help of Ruby, Robin, and Alice. Robin had a silly idea on what to wear, she and Alice had been watching all the 90s romcoms together. 

Robin suggested to Emma if she couldn’t think of anything to wear, then why not what Julia Robert’s character wore to her first opera in Pretty Woman. Emma laughed; she was just stupid enough to try this prank and see if Regina noticed. She spent the rest of the day trying to get as close as she could to the red dress and white gloves that Vivian Ward wore to impress Edward Lewis. And she booked a hair appointment to accomplish the elegant matching hairstyle from the movie. Emma borrowed Ruby’s reddest lipstick. Emma thought to herself, she had to have some fun on this opera date, or she was going to be bored to tears.

When Emma’s taxi pulled up in front of Lincoln Center, she felt a swarm of butterflies in her stomach; she hoped Regina didn’t hate the dress or look. She slowly got out of the cab and headed towards the main entrance. Emma got sight of Regina waiting for her by the doors. Whoa, Emma thought, she paused for a minute, taking in Regina in her flowing black sleeveless dress and plunging neckline. The dress was super classy and super hot. Emma swallowed hard. Damn, this woman looked good. She slightly picked up her flowing red gown and walked as gracefully as she could towards Regina.

Regina was just about to call Emma to ask if she was running late or if the blonde had indeed decided to ditch the boring opera she called it. She looked up and saw Emma gliding towards her in a gorgeous red dress that looked vaguely familiar. And it wasn’t just the dress. Emma’s hair was done up in an elaborate upsweep on top of her head. She was wearing a long, appealing evening gown that curved in all the right places and showed a considerable amount of cleavage. The dress was accompanied by long white gloves, covering her hands and forearms. Again, her memory pinged her; this red dress, long white gloves, and hairstyle looked familiar, like right out of a movie. Then it hit Regina why this all looked familiar; it was right out of a movie. Regina didn’t know whether to applaud or scold Emma; her date was cosplaying Vivian Ward from Pretty Woman.

Emma had a huge grin on her face as she did a small twirl showing off her dress and waiting for Regina’s reaction and hopefully, her approval.  
Regina’s expression was blank; she held onto her poker face. Yes, she knew this dress. She wondered if Zelena had bribed Emma to wear this romcom ensemble. She had seen that insipid movie to many times to count thanks to Zelena’s insistence they watch it again and again. Her sister would always stand up and yell, ‘Big mistake! Huge!’ during the shopping scene, usually knocking off anything in the near vicinity with her overdramatization. Regina would admit that Emma looked beyond her wildest dreams and nightmares; she feared the blonde would show up wearing those overalls or an entire dress made of pleather.

“Do I look okay?” Emma asked in a worried tone when Regina remained silent with a stern look on her face.

Regina stood speechless, Emma looked breathtaking, a real vision of beauty. Gone was the swashbuckler and now stood before her, the princess.

“Hmmm,” Regina kept her face serious as surveyed Emma’s attire, even though her body was betraying her, her insides were having quite the meltdown over this romcom recreation look. She wanted to run her hand over Emma’s smooth bare shoulders and slowly peel those gloves off.  
“Hmmm,” Emma mimicked Regina, she patted herself down in the dress and put her hands on her hips. She thought she had nailed it with the look, but maybe it was too much for this uptight Regina. She didn’t even know if Regina was going to get the reference and if she did, would she think she was crazy with too many romantic comedy leanings.

Regina’s eyes roamed up and down Emma’s dress; she squinted her eyes. She wanted to smirk, seeing the look of distress on Emma’s face. A slow, wide grin started to spread across her face; she could play along with this game.

“Something is missing.” Regina furrowed her brows.

Emma licked her lips and tried to hold down her huge grin. So Regina knew this movie just as well as she did. “Well, nothing else is going to fit into this dress. I’ll tell you that,” Emma patted her stomach and ran her hand over her tight garment.

Thankfully, Regina had decided to wear a necklace that only half suited her dress, she realized now it would accompany Emma’s dress far better. She reached behind and around her neck and unclasped the necklace. She slowly brought it down across her chest; she watched Emma’s eyes follow every motion with rapt attention.

“I don’t want you to get too excited; this is only a loan.” Regina moved to stand behind Emma. She lightly touched the nape of Emma’s neck and slid the jewelry over her skin. Regina clasped the necklace into place and thought she felt a shudder from Emma. She inhaled, Emma, smelled of something sweet and yet also flowery, it was a heady scent, Regina wanted more.

“Thanks Edward,” Emma ran her hand over the necklace and smiled at Regina.

Regina smiled at Emma; she felt her cheeks go warm despite the frigid temperatures of the evening.

“I didn’t even have to give you a blow job,” Emma tilted her head at Regina.

“And the moment is ruined and off script,” Regina rolled her eyes, she motioned for Emma to start walking towards the lobby doors. She watched Emma touch the necklace several times, then her gloves, the blonde indeed look like a fish out of water. “When you’re not fidgeting, you look very beautiful and very tall.” Regina straightened her back even more to reach Emma’s height but failed.

Emma grinned at Regina as they continued walking through the lobby. 

“You clean up nice too.”

Regina scoffed as if she ever had been dirty. They both could feel people’s eyes on them as the gracefully located their section of the theater near their box seats.

When they arrived to their box seats, Regina’s eyes went wide, and she scowled.

“What?” Emma looked to Regina, wondering what was wrong; she followed Regina’s eyes and saw the same redhead from the bar sitting next to what she assumed were their seats. “Do you know her?” She whispered to Regina.

“Yes,” Regina gritted through the teeth back to Emma.

“Regina, darling so unexpected to see you here tonight,” Zelena stood up and gave air kisses to each of Regina’s cheeks. “And you brought a date, even more unexpected.” Zelena’s eyes slowly traveled up and down Emma’s body. “Oh, she’s lovely. And she can do both overalls and Julia Roberts.”

The red head’s eyes were almost consuming as they trailed up and down Emma that she felt like she should cover herself with a shawl or something.

“Emma, this is my sister,” Regina said in a very surly tone. Clearly, not happy at all, her sister was attending the same opera. And not happy she was sitting next to them on their first date.

“Hey, thanks for the porn,” Emma reached over to shake Zelena’s hand. “And the bikini shot.”

Zelena reached up to shake Emma’s hand. “Yes, those were backups if my dear sister wasn’t sexting you enough.” She held onto Emma’s hand for too long, Regina reached over to unclasp their joined hands. “My sister’s idea of hard foreplay is shaking hands.”

Emma looked over to Regina, who rolled her eyes at Zelena. “Can we just sit down, please?”

Regina went to sit down and then realized Emma would be sitting next to Zelena, so she gently pulled up on Emma’s arm to switch seats with her. 

They sat in silence for a few moments, Regina stared ahead, and Emma glanced over at Regina and then Zelena who eyed at both of them, she kept winking at them. Emma wanted to laugh, but she didn’t think Regina would appreciate it; so far, this was one of the weirdest first dates she ever had been on. She wasn’t used to meeting someone’s family on a first date. Zelena was completely ignoring her male escort to focus entirely on her sister and Emma.

Both women took a deep breath when the opera finally started. Emma could feel Regina physically relax a little next to her. Emma had dreaded sitting and listening to the opera as soon as Regina had said they were going to the long-winded musical. Surprisingly, about twenty minutes into the opera, Emma found herself following along with the story and actually caring about the main character woman. However, she kept getting distracted by Regina’s sister.

Zelena kept nudging Regina’s arm; finally, Regina had enough and snapped to her sister in her most threatening whisper, “What? Stop it.”

“Regina, hold her hand for fuck’s sake…” Zelena swatted Regina’s arm again. “…or you might not get a fuck even for the sake of it.”

“Shhh,” Regina growled back to her boundaries breaking sister.

Zelena shoved Regina, which caused her to bump her shoulder slightly into Emma’s shoulder. Regina felt her cheeks redden, feeling her bare shoulder brush up against Emma’s bare shoulder.

“Just put your hand on her thigh,” Zelena whispered to Regina.

Regina wanted to crawl under her chair.

Emma wanted to laugh so hard, did the two sisters think no one could hear them. It was pretty cute how Regina’s sister was pestering her to try and make a move. The two sisters came across as battling toddlers, and Emma almost felt like the sought after toy. She decided to make it easy for Regina and get her sister off her back. Emma slowly and discreetly as she could, rolled down her long white glove, and removed it from her hand. She reached over and ran her hand down Regina’s forearm slowly, stopping briefly to caress Regina’s hand on their shared armrest then kept going down, pushing her palm over Regina’s palm and intertwining their fingers slowly.

Regina took a loud gulp; Emma’s thumb slowly caressed her thumb back and forth, leaving a warm feeling all over her body.

Okay, so Emma thought, maybe handholding was hard foreplay. She didn’t want to admit to anyone that just holding Regina’s was making fluids release all over her body.

“Jesus… I’m going to need a cigarette now.” Zelena blurted out way too loud, a few opera-goers from the next box seat over ‘Shhhed’ her. “I might have a stroke if tongue kissing happens next.”

It was hard to stay mad at Zelena when Emma’s thumb kept caressing her hand, Regina kept imagining that thumb caressing a lower part of her anatomy. She couldn’t focus on the opera at all, just Emma’s hand. It felt like her hand held a hypnotic spell over her whole body, scorching magic coursing through her veins and bottoming out in her vagina. She was surprised when Emma pulled her hand away and looked up to see everyone to give a standing ovation to the end of the opera. Regina realized she had never zoned out of a performance in quite that way before; she turned her head away from Emma to her libido back under control. She didn’t bother to look at her sister; she knew she would be grinning like the mad joker character.

Emma was glad when they finally reached the front entrance when a wave of chilly air hit her skin; she hoped it cool down her insides as well. And she was thankful Regina’s sister finally took an interest in her escort and waved them goodbye and left them alone out in front of the theater. Regina had a car brought around for her and Emma. As soon as they were in the car, Emma had to ask.

“So, what exactly is your sister’s strategy here?” Emma smirked; she didn’t want to say out loud what she thought the strategy was to embarrass Regina further.

“My sister thinks it’s been too long since I dated…” Regina found it hard to make eye contact with Emma on the next part, “…and grew physically close to someone.”

Exactly what Emma thought, she smiled warmly at Regina. She was glad they were sitting side by side so Regina could look at the window if she wanted.

“Regina, go at your own pace. Don’t let your sister push you. I’m not in a rush…” Emma realized that sounded a bit presumptuous, what if Regina wasn’t attracted to her and just wanted to get through the ten dates to win her sister’s bet. “I mean…that is if you are interested in not rushing with me?” 

Ugh, Emma thought, she sounded kind of lame right now; her smooth-talking skills had utterly abandoned her. Sure, she thought, not rushing and prolonging the dates as long as possible to get to three months was the goal; however, seeing Regina in this black dress made Emma wondered just how much she truly missed her beloved bug car. No, she shook her head, Ruby was not getting her car baby, she could do this, she could turn off her libido and properly woo and be in a regular relationship for three months or ten dates, whatever came sooner.

Emma decided to try a line from the movie to lighten the mood, so she reached out again for Regina’s hand. Both sets of hands had gotten a bit chilled from the walk to the theater to the car; they were warming up fast in each other’s grasp. “If I forget to tell you later, I had a really good time tonight.” Emma turned her head to stare into Regina’s eyes; the brunette had turned back to look at Emma.

“Thank you,” Regina reprising her Edward part with a sly smile. She broke eye contact and looked down at their shoes. Emma again matched the costume perfectly from the movie. “You’re not in a rush? But you will be.” 

Regina knew in this fast sex on the go like any food being delivered to your door at any time of the day or night by an app, taking it slow was outdated and old fashioned. 

Emma was torn, she usually would be a little impatient, but thanks to Ruby’s rule, she was being forced to be patient. And Regina could be fun if tonight was anything to go by and that erotic handholding.

“I’m not in a big hurry, isn’t that the new life motto? Slow down, be present? Take a lot of deep breathes?” Emma playfully squeezed Regina’s hand. “If neither of us wants to get physical right away, we don’t have to…unless Zelena has tapped into our phones and is spying on us.”

Emma could see Regina’s fear in her eyes; she decided to cut this off early. “Regina, you’re the most beautiful…stunning…weird…irritating woman I have gone out with, and it’s only been about a date and a half.” 

Regina squinted her eyes at Emma. “I’m counting our awkward car ride and endless streaming messages as a half date.” She could see Regina relax a little bit.

Regina looked back up into Emma’s eyes. She felt ridiculous now; she was a powerhouse at work, people feared and loathed her, and here she was feeling, what the hell was she feeling she thought, scared? Scared of this swashbuckling princess.

“We’ve got nine dates left to go; there is no race; there’s no finish line. I’m not even sure what happens after ten dates. Do you turn into a frog?” Emma smirked at Regina.

“No, you do.”

The car pulled up to Emma’s building.

“Thanks for the ride home,” Emma leaned over and gently raised Regina’s hand to kiss it goodnight. She thought, why not pull out some other hand romantic clichés.

Regina watched Emma with confused eyes. Emma’s lips on her hand send jolts through her body, goosebumps sprung up along her arm.

“You’re right, and I never realized how erotic handshakes could be, I’m going to take a long cold shower or maybe a quick hot one.”

Regina smiled and withdrew her hand from Emma’s hold.

“See you for date two?” Emma asked, then added in a low husky voice, “It’s my pick for anything I absolutely want…so be prepared.”

Regina felt heatwave sweep through her body, hearing Emma’s voice low and deep.

“Why am I envisioning being forced to partake in mud wrestling or something equally vulgar in that vein?” Regina replied, in her own, and she thought a better sexy voice.

“That is an excellent idea.” Emma wanted to fan herself; she felt herself overheating, hearing Regina’s what could only be called the seductive voice she’s ever heard in her life. Lord help her keep the chastity side of Ruby’s bet much longer if Regina kept using that voice on her. Or anyone in the near vicinity, that voice was having a strong desired effect on her libido.

“No, it’s not.” Regina watched Emma exit the car and turn to wave goodbye to her. She realized that she was strangely excited to see what Emma would pick for their date two.


	3. Date 2

As turned out, the two women had very demanding work schedules, and finding time for date two was a challenge. Emma didn’t mind much because, in Ruby’s eyes, it looked like she was dating Regina longer. Although Emma knew she was going to have to cancel some work commitments to make time for date two. She might not have known Regina very well, but Emma realized she had two objectives now in regards to these ten dates. Objective one was to win this bet and get her car back. Objective two was to get to know Regina better because date one had been kind of fun. So to ensure both objectives, she was going to have to take some work breaks so she could date Regina. And that specifically meant making time to plan a date that Regina might like and enjoy to ensure there would be seven more dates.

Regina smirked when she got Emma’s text on where to meet for their second date. She knew it would be sport-related, and then her smirk turned into a genuine smile because it had been ages since she had attended a baseball game. She admitted to herself; she had been looking forward all week to the game and seeing Emma again. The date at the opera, while mildly fun and interesting, had also been annoying since Zelena crashed it. The nicest part was when Emma held her hand. She thought about the hand holding a lot over the week as if it was some 18th-century porn that made her flush and sent warm tingles throughout her body. She told herself to get a grip; it was just handholding.

When Regina walked around the street corner and saw Emma waiting out front of the stadium for her wearing jeans and a baseball jersey, she tried to squash the airy feeling in her stomach. She was just excited for some good stadium junk food; it had nothing to do with Emma. And nothing to do with the fact the blonde managed to pull off sexy and cute in a baseball jersey at the same time.

When Emma first spotted Regina as she walked towards her, she had to reign in her libido. The brunette woman looked so hot in jeans and a low cut Met’s t-shirt with a baseball hat on to top off the ensemble. She thought to herself; this look was even sexier than the gorgeous dress from their last date. Although, she realized Regina could make anything look good, probably even a garbage bag.

“You really batter up,” Emma smiled as her eyes trailed up and down Regina’s more casual look. She swung the large bag over her shoulder to her other shoulder.

Regina allowed her eyes to do the same, sweeping over the blonde a few times. “Aren’t you a Mets fan? Why the blank jersey?” She eyed Emma’s shirt more closely if she wasn’t mistaken, the shirt almost looked like a pajama shirt.

“I am, just forgot,” Emma said quickly as she moved in front of Regina to usher her inside. “Shall we?”

As the two women wandered the stadium locating their seats, the smells of fried food, beer, sweat, and the sun hit Regina’s nostrils, and she couldn’t contain a smile.

“I knew it would be sports,” Regina lowered herself in her seat slowly, she loved baseball but wasn’t a fan of the hard seats.

“Oh wait,” Emma reached in her large bag, “I got these dorky things...if you want one.” She showed Regina a seat cushion.

Regina didn’t think a seat cushion could be used as a wooing device, yet here she was a little impressed with Emma’s notion to help bring her ass some comfort.

“Hey, we can’t have you getting a sore butt,” Emma smiled up at Regina, then added a little softer and in a lower voice, “well, at least not from this.”

Regina whipped her head around to Emma; did she just say something about sore butts? She squinted her eyes at the blonde, but she had her head turned towards the field. Oh great, Regina thought, now instead of handholding, she was going to think of some kind of variation of butt holding or butt touching. She shook her head, being in the close proximity of Emma again was making her hormones increase and go a bit wild.

Emma had turned her head after the butt comment; she realized she might have said it loud enough for Regina to hear. She felt warmth hitting her face, so she tried to stop thinking of butts, specifically Regina’s butt, and what it would look like naked or perhaps pressed up a glass window. 

“Well, I thought of torturing you with mud wrestling or laser tag, but I’m lazy, baseball was just easier.” She shrugged.

“So you’re a big Mets fan?” Regina had a suspicion in just the way Emma seemed a little awkward in her seat, staring out over the baseball field, the way the blonde was utterly lost finding their way around the stadium; it was as if she had never been to a game here before.

Emma nodded aggressively, “Yeah…love them.”

Regina watched her with curious eyes, “Who’s your favorite player?”

Emma looked around the field then motioned with her hand in a wide fashion, “I love the whole team.” She turned her head to Regina who kept waiting, “But if I had to pick one player then…” she craned her head back and forth across the baseball field, “…that guy.” Emma nodded as she vaguely pointed to the baseball field.

Regina couldn’t hold down a smile, Emma didn’t know anything about baseball.

“Have you ever been to a baseball game?”

“Of course I have, I love sports,” Emma realized maybe this was an excellent time to get some drinks and snacks to avoid answering any more questions and her lack of knowledge of them.

“Hmmm, how many innings are there?” Regina raised her eyebrows to Emma.

“Twelve? I mean twelve.” Emma stated more firmly.

For some reason, Emma not knowing anything about baseball made her more endearing to Regina.

“Why did you pick a baseball game?” Regina turned her head to stare at Emma with furrowed brows; she wanted to know the answer to this question.

Emma turned her head to stare into Regina’s eyes; they held each other’s gaze, both feeling a pull. Then before the pull could turn into something more of a glaze or pressing of lips, Emma’s eyes shifted upwards when two figures were approaching their aisle.

“Oh fuck me…” Emma’s eyes rose up and looked to the steps behind Regina.

Regina felt herself flush at Emma’s language, yes she was heading that way towards the blonde very quickly, yet she had a feeling that Emma wasn’t talking to her anymore. She turned and saw what Emma was glaring at; a long dark-haired and blonde woman were standing next to their aisle.

“What the hell are you doing here?” Emma growled out to the long dark-haired woman and blonde women smiling behind her.

“Alice and I wanted to see the game; I can’t believe you’re here,” Ruby put her hand on her chest in fake mock surprise.

“Bullshit,” Emma spat out.

There were two seats next to Regina on the aisle, so Alice sat next to Regina. Ruby crawled over Alice, Regina, and Emma rather clumsily while landing on both of their laps momentarily to sit on the opposite side, making a sandwich of Regina and Emma.

“What have we missed so far?” Ruby asked Regina and Emma; she raised her eyebrows suggestively towards the blonde.

“There was a beach ball tossed around,” Emma gritted through her teeth as she snapped at Ruby.

“Hi, I’m Ruby, and that is Alice,” Ruby reached over Emma to shake Regina’s hand, she made a motion of elbowing Emma in the gut. Emma gave out a little yelp.

“Pleasure to meet you two, I’m Regina,” Regina shook Ruby’s hand then Alice next to her. “How do you know Emma? Also, baseball enthusiasts?”

Emma turned her head and shook her head, why had Ruby showed up, that wasn’t fair in the bet. She had a feeling she was going to sabotage her in some way so Regina would stop their dates. Ruby could play dirty sometimes; Emma had to make sure to limit their interaction.

Ruby leaned over and whispered in Emma’s ear, “Dude, put your arm around her.”

“Stop it,” Emma hissed back to Ruby, trying to stay quiet as not draw attention to their conversation.

Ruby started asking Regina questions about the game, while also nudging Emma to put her arm around Regina’s chair. Emma kept jabbing her elbow to get Ruby to back off.

Suddenly, Emma jumped out of her chair after Ruby pinched her. “I’m going for snacks,” Emma announced loudly, she wanted to get away from Ruby and take Regina with her.

“I’ll help you,” Ruby offered up fast.

“No!” Emma spat back to Ruby, squinting her eyes hard at the long-haired brunette. “No, thank you.”

“Regina, wanna come with me to get drinks?” Emma blurted out and interrupted their talking.

Regina looked startled, “Uh, sure.”

“You stay put Regina; you’re the only one that actually knows what’s going on in the game. I’ll help you, Swan.” Ruby smirked to Emma.

Emma rolled her eyes as she stomped up the steps and towards the snack bar. She figured, leaving Alice alone with Regina was mostly harmless.

As soon as they were out of earshot of the seats, Ruby started in. “So waiting until later to pull out all the signature Swan moves?”

Emma scoffed, “I don’t have signature Swan moves.” She thought to herself, so okay, she had some charms that usually worked on some women, but none would work on a woman like Regina. She got at the end of the snack bar line of the large stadium.

“Please, I can’t believe she’s not sitting in your lap already…” Ruby got in line next to Emma, “…or with Regina, I see you sitting in her lap,” Ruby laughed at her own joke.

“Ruby, stop it. I’m trying to get to know Regina. Remember you said I had to date her for three months, I don’t want to…burn out too soon.” Emma hoped no one was listening to their conversation in line.

“True, you probably don’t have much stamina,” Ruby crossed her arms over her chest.

“Hey, I have plenty of stamina,” Emma cringed when she realized how loud she said this statement, a few people looked her way, and one woman winked at her.

“Just don’t be too standoffish Swan, women wanna know if you like them or not. You know what I’m saying,” Ruby had a mischievous glint in her eyes, yes she knew she was messing with Emma, sometimes it was just much fun. And sometimes payback was an asshole, sometimes an attractive friend but still an asshole.

“You’re the one who is putting restrictions on me like I’m gropey McSwan or something. This is getting into my head, I’m almost afraid to touch her,” Emma tried to lower her voice now.

They got their turn at the snack bar and loaded up with hot dogs, chips, popcorn, and beers. As they started walking back to their seats, Ruby couldn’t resist teasing Emma some more.

“Well, don’t worry, we’ll all witness a big smooth today.” Ruby raised her eyebrows suggestively to Emma.

“What? Why?” Emma asked of her frenemy; she started to get a weird feeling. “Where’s Robyn? Why is she not with Alice?” When the young blonde love bird couple was separated, they were usually up to no good.

Ruby grinned, and Emma felt her stomach tighten in a bad way. Emma grabbed Ruby’s beer from her hand and threw it in the trash and ran back towards their seats to warn Regina or maybe convince her to leave the game before whatever Ruby was planning happened.

Regina was engrossed in the game and talking to Alice. Emma pulled up her and whispered in her ear. “I think Ruby is going to prank on us, follow my lead. Don’t do whatever she wants.”

When Ruby finally returned after waiting in the snack bar line again, she scowled at Emma. “Real nice Swan, that line was twice as long when I went back to get another beer.” Emma just gave Ruby a fake plastic smile.

The game went on, and Emma kept waiting for something to happen, her eyes bounced nervously around searching the whole stadium for anything coming. Her fingers clenched against her jean, clad thighs. She had no idea what Ruby was planning, but she knew she wasn’t going to like it. The game dragged on, and in between innings, the announcer blared over the speakers.

“OKAY EVERYBODY IT’S KISS CAM TIME!”

Huey Lewis and the News’s song ‘Power of Love’ started playing, and on the jumbotron, people all over the stadium were being singled out to kiss on camera.

Emma scowled; Ruby was going to force Emma to kiss Regina in front of everybody. She wanted to kiss Regina on their terms, whenever the magical moment might happen. Emma winced, had she thought that? Did she compare a kiss to a magical moment? Emma hoped Regina realized what her warning could have meant this; she didn’t want Ruby to her get their kiss on the kiss cam. She looked over quickly to Regina her, tilted her head, and nodded.

Suddenly, the Kiss Cam was on Regina and Emma. They both look startled on the big screen; there were cheers and yelling around them. 

“KISS! KISS! KISS!”

Emma stared at Regina with wide eyes, and the brunette took a sip of her beer and then raised her glass over her head as a toast. People booed! Emma smiled and clapped; thank goodness Regina was playing along.

The Kiss Cam moved onto another couple as some people shouted, ‘That’s homophobia!’ ‘Let the hot chicks kiss!’ ‘Do your job!’ Emma looked baffled, it was like getting a live feed of a comment section on an article she didn’t want to read and let alone hear people’s opinions.

Ruby glared at Emma, then nodded to Alice, who frantically started texting on her phone.

“WHO’S NEXT?” The announcer declared as the Kiss Cam moved on from Regina and Emma.

Emma took a deep breath and slumped into her chair, almost scooting off the seat cushion. Regina smiled at Emma, then suddenly, people were yelling at them again.

“BACK TO OUR FIRST COUPLE TO RECONSIDER!” The announced yelled over the massive speaker system.

Emma wanted to smack Ruby for this kiss cam obstacle. Then she looked up, and the Mets mascot was standing behind them, cheering for her and Regina to kiss. She bolted up in her chair, knocking the seat cushion to the floor. The Mets mascot with a huge baseball head was clapping and pointing at her and Regina. She looked over to Regina, who rolled her eyes.

Emma pulled on one of the arms of the Mets mascot and pulled them down to their seats; then, both her and Regina each kissed a side of the baseball head mascot costume.

More loud boos came from the crowd for the mascot kiss instead of a real kiss from the elusive hot couple. The mascot waved their hands in defeat and walked away from Regina and Emma. The Kiss Cam continued on harassing more couples and non-couples. 

Then before Regina and Emma could relax, the announced yelled again, “ONE MORE TIME FOR THAT LOVE AT FIRST SIGHT COUPLE! WHO’S ON THEIR FIRST DATE!”

Emma pursued her lips; she was definitely going to get Ruby later for this one. “Really??”

The Kiss Cam was on Regina and Emma again. The cheering and chanting started up again, “KISS! KISS! KISS!” “END HOMOPHOBIA!”

Emma nodded to Regina and gave her a slight head tilt. They both turned around in their seats quickly and before Ruby and Alice could figure out what was happening. Regina landed a big kiss on Alice’s lips, and Emma smacked a big smooch on Ruby’s mouth.

There was a mix of boos and cheers! ‘NICE KEEP THINGS OPEN!’ ‘YAS QUEEN!’ ‘GOALS!’ Someone yelled.

Even though Regina had her head turned while kissing Alice, she managed to extend her arm over Emma and dump her beer in Ruby’s lap.

Ruby jumped up out of her seat, breaking off the impromptu kiss with Emma as the cold beer poured all over her lap.

Regina gave a wicked smile as she broke off the quick, awkward kiss with Alice to admire her work of soaking Ruby’s jean shorts. She didn’t like the visual of Emma kissing another woman, so she thought this was good payback for the prank and the mental photo she wanted to delete. She stood up and gathered her purse to leave; she looked down at Emma, who had a beaming smile pointed up at her.

Emma looked down at Ruby’s wet jean shorts, a smirk spread across her lips as Ruby’s visibly reddened face met hers. “I know I’m a good kisser, but that’s kind of embarrassing,” Emma winked cheekily and stood up to join Regina.

“Robyn is not going to be happy,” Alice mumbled out as Regina and Emma got to the end of the aisle.

“Good luck with that,” Emma put her hand on Alice’s shoulder.

As soon as they walked out of the stadium, Emma broke the silence that had engulfed her and Regina. “Sorry about all that. My friends are very immature and idiots.”

Regina nodded and smiled at Emma as they walked along the sidewalk. 

“Well, as you experienced last week, so is my sister so I guess we’re…”

Emma wanted to guess Regina’s next word, so she jumped in, “Unlucky? Cursed?” She then took a deep breath, added softer, “Compatible?”

Both women stopped on the sidewalk and looked into each other’s eyes.

“Emma…” Regina didn’t know how to ask this question, she bit her lower lip and wrung her hands together, “…do you not want to kiss me?” Regina didn’t care they were on the busy sidewalk, and soon it would be even more crowded after the game finished. She wanted to know why the charade of not kissing on the kiss cam. She wanted to know now because if Emma didn’t want to kiss her, then they wouldn’t make it date three.

“No!” Emma shook her head fast, getting the wording wrong. “I mean Yes! Yes, I want to kiss you!” Emma shouted this loud, and a few people on the street stared at the two women, she thought she heard a ‘Get it girl!’. 

Emma stared hungrily at Regina’s lips. “I know it’s only our second date, so I didn’t want to seem forward, but actually…” Regina watched her closely, “…I wanted to kiss you even though you annoyed me at the bar, and I wanted to tongue kiss you in places…”

“That’s a bit forward,” Regina raised her hand to stop Emma while being completely turned on and affected by the blonde’s words. If Emma had finished, she didn’t know if she was going to be able to make it back to her apartment without pulling the blonde into an alley and having a quickie or perhaps a very long one.

“Sorry, I just didn’t want our first kiss to be on a silly kiss cam in front of everybody.” Emma reached for Regina’s hand; they felt so warm and soft. Damn, she thought, this handholding is turning me on. “I just wanted it to be kind of special or unique.”

Regina gave Emma a smirk, she did like the slow approach, and she ignored Zelena’s voice in her head to go faster. She grabbed onto Emma’s hand, and they continued holding hands and even interlocking their fingers as they walked down the street. When they finally came to the corner where they had to part to go their separate ways, Regina thought about what Emma said, and she didn’t want a rushed first kiss even though she kind of desperately wanted to feel the blonde’s lips on hers. So she leaned and pressed her lips firmly and lingered on Emma’s cheek. Regina also took a moment to inhale Emma’s scent, which was a mixture cinnamon and something playful that she couldn’t put her nose on. Regina was pleased when she heard a small gasp from Emma, and when she reluctantly pulled away, Emma squeezed her hand harder. As Regina was about to turn away, Emma grabbed hold of her hand again, leaned in and kissed her cheek slowly and inhaled, she smelled apples and something sinful she couldn’t put her nose on. Regain didn’t want to admit her knees felt a little weak from a cheek kiss.

“So, you’re going to torture me with more opera for date three?” Emma held onto Regina’s hand. Once again, Emma found herself wanting to find reassurance there was going to be another date, especially since Ruby and Alice crashed their second date. Why was her heart beating so fast? It was just a date, okay, so maybe getting the car back meant more to her than she thought. And so did maybe Regina taking her on another date.

“Possibly.” Regina looked down at their joined hands and rubbed her thumb over Emma’s finger. “Or what about one of those pottery classes?”

Emma tried to hide her disappointment; she didn’t want to make garbage she wasn’t going to use.

“Sure.” Emma nodded her head anyway because it meant doing something Regina enjoyed, then it was probably going to be okay. She didn’t care for opera or baseball. Yet, both outings have been pretty decent because it was turning out the uptight woman before her was fun no matter what the activity.

“I’ll check my calendar and get back to you,” Regina almost purred to Emma as she squeezed her hand and pulled away from the blonde.

Emma said goodbye to Regina and bumped into a traffic pole, trying to cross the street. Regina smirked then nearly fell down stepping into a pothole while crossing the adjacent street.


	4. Date 3

Another busy work week went by with Regina and Emma texting and trying to coordinate a time to meet up for date three. Regina admitted to herself one night trying to fall asleep that she was a little disappointed the baseball game outing date hadn’t ended in a kiss. She didn’t enjoy kissing Emma’s friend Alice; she wanted to kiss the main blonde. Yet Regina did like the slow approach Emma was going; she had seven dates to go, so there was time to win Zelena’s bet. Just as long as they started getting a tad more intimate, she felt confident that she could win this silly bet.

Emma was surprising in some aspects; she turned out not to be a sports fan, the only reason Regina could think of why they went to a baseball game was somehow the blonde found out she likes baseball. She wanted to find out something Emma liked to plan their next date, but then a new merger happened at work, and it left her scrambling to sleep and eat barely. Instead, she suggested taking in the new exhibit at the Metropolitan and was surprised that Emma agreed graciously. Maybe the blonde was more of an art lover than a sports fan.

For some reason, Regina felt flustered when she saw Emma again, her palms started to sweat, and her stomach felt weird. Regina shook her head, this is a fling, and these physical manifestations were indications she was getting attached to this blonde already. She thought maybe her obnoxious sister was right; she pushed Zelena and her awful theories from her mind and instead focused on Emma smiling at her. For someone who seemed to date a lot, Emma didn’t seem very smooth, which in return made Regina’s stomach feel even weirder. The blonde awkwardly hugged her and said hi three times.

“Thanks for coming to the museum to see the new exhibit,” Regina fidgeted with her purse over her shoulder. “Hope you don’t mind, it’s kind of a work research thing too.” She slowly raised her eyes to look at Emma.

“Multi-tasking…it’s kind of hot.” Emma licked her lips; she should be annoyed that Regina was double-booking their date, yet she was impressed. Emma shoved her hands in her jean pockets. “I was disappointed you didn’t pick roller derby, but we can have fun here too.”

“Plan on skating through the museum like Steve Martin in that one movie?” Regina smirked at her as she led the way into the museum. She was a little relieved that Emma wasn’t mad about her work research.

“Why didn’t I bring skates?” Emma made a motion to smack her head. 

“No, actually every time I’m here, I work on my cat count.”

Regina stopped walking and turned to stare at Emma with raised eyebrows. “I don’t want to know what a cat count is do I?”

Emma moved closer to Regina and placed her hand on the small of Regina’s back; she led her over to a very old painting. At this gesture, Regina felt like she could get behind whatever a cat count was, the feel of Emma’s hand on her back felt entirely too good.

“These old paintings are so biased; there are way more dogs than cats.”

“You seem more like a dog person,” Regina whispered back to Emma, still enjoying her hand on her back.

“Well, maybe I am, but I don’t want cats getting neglected from art and history,” Emma said a little too loud. She noticed she couldn’t seem to take her hand away from Regina’s back. “Cats are freaking cool; they are the cutest assholes.”

“Shhh, keep your voice down on this silly cat crusade.” Regina leaned and whispered in Emma’s ear, she wanted to graze her cheek against Emma’s or perhaps nibble her earlobe but refrained. She tried for a stern look when she pulled slightly back to stare in Emma’s eyes but couldn’t help the grin spreading across her lips, probably had to do with the blonde’s hand still on her back.

Emma reluctantly pulled her hand away from Regina’s back, again she didn’t want to seem too handsy. Her brain told her it was still only date three, so maybe bring it down a notch. Her body, however, was not used to being this slowed down. Emma had to scold herself from being so turned on by a simple touch. She told herself to focus on the task at hand and throw a mental cold shower on her libido.

There was a painting before them of some old scene with men making some kind of business deal in a back alley at a table with a dog looking on with concern.

“Look at this one, if anyone is going to be throwing shade at these men, I think it would be a cat and well probably a dog too because what in the hell is with that guy’s pink bow at the back of his jacket?” Emma motioned to the absurd big bow in the painting. Then her hand went lower over the painting. “And that jug? Is it booze or urine?” Emma scrunched up her face.

“Clearly, you live in the right time period. I don’t think you would have enjoyed living in the 15th century or in a forest.” Regina moved onto the next painting, yet her eyes sparkled as they looked at the disgust on Emma’s face.

“Fuck no…” Emma almost gagged.

They walked a little further into the museum when Emma’s eyes lit up.

“Oh, this is my favorite…” Emma said softly while gently pulling Regina to stand in front of one particular painting.

The painting was of a child in some of frilly jazzy jumpsuit holding a string while a bird ate what looked like a credit card, and three cats next to the child completely wide eyed, were obviously contemplating the bird as their main entree on their dinner menu.

“Now this one is a classic, there’s not one but THREE cats in this painting,” Emma pointed to the two cats in the lower half of the painting.

“It seems we have hit a jackpot with this painting,” Regina stood admiring the painting, although she feared what happened later in the world of the painting, the poor bird.

“Pretty sure I saw someone wearing that similar jumpsuit around Chelsea last week,” Emma turned to look at Regina, then it hit her, what Regina had just said. “You said we? Are you fully on board for the cat count game now?” She smiled at Regina.

As they kept walking throughout the museum, they would brush shoulders and arms. Finally, Emma grabbed Regina’s hand and held on as they strolled along the paintings and sculptures. Regina indeed found herself swept up in Emma’s cat count game and the warmth radiating through her body, steaming from Emma holding her hand.

“Oh!” Regina said rather too loudly, a security guard gave her a stern look and shushed her. She felt her cheeks reddened at her outburst, her excitement of spotting another cat in a painting and alerting an oblivious Emma. She pulled Emma to stand in front of a new acquisition to the museum.

The painting was of two kids teasing a cat with scorpions. Emma looked baffled and horrified; her mouth hung open, and her eyes squinted.  
“What the hell is going on in this painting?” Emma exclaimed loudly, getting another ‘shush’ from a different guard and a stern warning look.

“Sorry, all I saw was the cat…this is disturbing,” Regina looked at the painting and tilted her head.

“I want to reach into the painting and save that cat. Hope that cat smacked the shit out of those mean kids,” Emma furrowed her brows and crossed her arms against her chest.

Regina grabbed ahold of Emma’s hand again, about to lean in and perhaps be bold and kiss away that awful painting. Regina’s phone started vibrating. A lot. Emma raised her eyebrows and looked down at the device in Regina’s hands. Regina let out a deep sigh and started texting.

“I’m sorry. I need to go; there is a work emergency,” Regina stared into Emma’s eyes, looking for some kind of forgiveness.

Emma shrugged, she was disappointed Regina had to leave before they could get their cat count up higher and was even more disappointed she didn’t get to spend more time with her.

“Are you still up for date four? Your pick. Whatever you want,” Regina purred the last part; she hoped she got her message across to Emma.

Emma fully understood ‘getting the vapors’ meant after hearing Regina purr ‘whatever you want’ in her ear, she could feel Regina’s warm breath on her neck, and it was an electric jolt to her core. Emma needed to fan her face and crotch area. She tried to get hold of her senses to reply.

“Well, we bought the Groupon, so we get ten dates for one.” Emma offered her best reassuring smile. “I’m not usually a cheapskate, but I don’t want to lose out on my Groupon.” Emma leaned in, standing so close to Regina they’re bodies were almost flush up against each other. She gazed into Regina’s eyes and whispered since the guards were still watching them again. “I want ALL ten dates.”

Being that physically close to Regina and not touching her was making Emma giddy, she could feel her pulse quicken, her throat went dry, and her hands itched to reach and touch the brunette.

So much warmth flooded Regina’s body, it felt someone switched on a massive Christmas tree inside her chest.

“Me too,” Regina leaned up and kissed the corner of Emma’s mouth. Her lips lingered as they pressed warmly onto Emma. She slowly started backing away from Emma and heading towards the exit while maintaining eye contact.

“Really? You had to kiss me in front of the cat being bullied painting?” 

Emma shoved her hands into her jean pockets and watched Regina walk away. Her mouth tingled where Regina had pressed her lips against the corner of her mouth. She might have to pick sex as her date night activity; sex counted as a date night activity, right?


	5. Date 4

As in the previous weeks, work became frenzied and chaotic for both women. The only small breaks Emma enjoyed were getting messages from Regina. The only reprieve that Regina looked forward to were messages from Emma. Finally, Emma made room in her schedule and made plans for date four; eventually, they found a suitable night in regards to both of their chaotic work commitments. And Regina made sure to keep her phone with her at all times so Zelena wouldn’t steal it again.

Since Regina had used their two dates as work research, multi-tasking at her smoothest, Emma realized she might need to do the same thing. And that’s how Emma ends up waiting outside an auditorium at a midtown community college for Regina. She’s not sure how Regina will take to this activity, she knew Regina was going to like baseball since some brief text messages to her sister let her know of her interest. And for the record, Zelena reached out to Emma’ on accident’ or as she called it a ‘butt text.’ A ‘butt text’ that was very long that also included borderline pornographic photos of Regina’s hands. Emma had to hand it to Zelena (pun intended), which was a bold yet effective move. Emma didn’t want to admit how long or often she stared at the photos of Regina’s hands, specifically her fingers. Regina had very nice strong hands, and all she could think of after seeing her beautiful fingers was how she could put them to excellent use.

Emma felt like a grinning idiot when Regina rounded the street corner heading towards her in workout gear. Once again, she needed to reign in her libido because Regina looked even more amazing in workout gear than she did in a fancy opera dress.

When Regina caught sight of Emma, her stomach did that annoying airy swarming butterflies thing that had been happening when she got a message from the blonde. Her eyes raked over the workout ensemble Emma was wearing, some kind of athletic pants with a stripe going down the legs, a white tank top under the hoodie; it was still rather chilly outside. Over her shoulder was a huge duffle bag that looked quite heavy.

“So, are you going to reveal the mystery of what we’re doing now? I came prepared as you see,” Regina motioned her hands up and down her workout ensemble.

“Indeed you did,” Emma licked her lips while her eyes roamed up and down Regina’s body.

Regina’s cheeks reddened, she felt a jolt of electricity surge through her body watching Emma’s eyes stare at her like she was a box of donuts after having been on a cleanse for too long.

Emma reached out and grabbed Regina’s hand to pull her along towards the building. Emma looked down at their hands; she never held hands as much as she had with Regina; their hands felt good together.

As soon as they entered the massive gymnasium type room, Regina was surprised and not really shocked by Emma’s choice of the night’s activity.

“Roller derby…you do not disappoint Miss Swan,” Regina smirked at Emma, although she didn’t quite get their attire and seats in the stands were empty. “Although I’m a little confused.”

“This is roller derby boot camp,” Emma raised her eyebrows with a wide grin to Regina.

“You want us to participate in roller derby?” Regina asked in a slightly stunned tone.

“You look like you could get some aggression out. Pretend everybody is Zelena.” Emma winked at Regina.

“I can think of other ways of getting my aggression out, but if you prefer my channeling that into other women, so be it,” Regina tried to sound cocky even though she was scared shitless to try roller derby. And she knew there was only one woman right now she wanted to channel any physical activity onto and that was a scary thought too.

Emma stood motionless for a second after hearing Regina, she better not pick up a roller derby chick tonight, she’s mine for seven more dates. The blonde stunned herself when she realized what she just thought; this bet was playing with her head. She shook her head to loosen the possessive thought.

“I went to the recommended Five Stride Skate shop and got us all the necessary equipment.” Emma patted the large bag over her shoulder; she then led Regina over to one of the benches and instructed her to sit down. Regina followed Emma with slightly larger eyes, as she looked around at all the women suiting for roller derby practice.

“Glad you dressed appropriately,” Emma watched Regina unzip and take off her hoodie and revealed her black tank top, showing off toned arms and very sexy collarbone. Emma shook her head, she had to calm down over Regina’s collarbone and well all of Regina in work out gear.

“You told me to dress like I’m going to hot yoga. I thought we were going to hot yoga, or perhaps you were going to insist on goat yoga,” Regina piled her belongings on the bench next to her. “I was prepared for a goat to stand on my back.”

“Well, if you want later, I can stand on your back and go bahhh,” Emma grinned at Regina as she made her best goat impression, then she turned her attention to pulling out all the equipment from the bag. “Okay, let’s get you suited up.”

Emma squatted down in front of Regina and began to unlace her shoes. As if she was some prince charming about to try the true love shoe test.

Regina’s face flushed; she was having a whirlwind of hot flashes through her body, having Emma kneel before her and taking off her shoes. “I can…take off my own shoes,” she barely stammered out.

“No worries, I’m already down here,” Emma had to squash the thoughts of just how far down Regina’s body she wanted to go. She gently took Regina’s sneakers off, then reached for the kneepads and slipped Regina’s foot through and pushed it up and around her knee. Emma loved having her hands on Regina’s body; the main reason she volunteered to suit up the brunette. The other leg was; next, this time, Emma went even slower, letting her fingers linger around Regina’s calf muscle.

Regina couldn’t help but shudder having Emma run her hands run slowly up her leg to adjust the kneepads. As soon as both kneepads were in place, Emma leaned over and brought the skates from the bag.

“Four-wheel roller skates, cool, huh?” Emma had a dopey smile on her face that was contagious. Once again, she gently picked up Regina’s foot and slid it inside the skate.

The prince charming shoe vibes were getting to Regina, so she put her hand on top of Emma’s. “I can lace them up…” Regina looked up into Emma’s eyes, “…you need to do your kneepads and skates too.”

Emma nodded her head; she did need to get her gear on and not have some kind of foreplay with getting safety gear on. Her overzealous hormones were getting out of control. She handed off the elbow pads to Regina and wrist guards. She knew putting on the wrist guards were too risky after staring at Regina hand photos for ages; she realized she needed to get a grip. Getting some hardcore exercise would hopefully burn off some of this sexual energy. However, seeing Regina in tight yoga pants and a tank top was not helping at all.

When both women stood up on their skates and the safety gear in place, Emma stopped Regina before joining the others in the class.

“Forgot one thing,” Emma reached into the bag and pulled out two brand new mouth guards. She opened the packet and stared at Regina’s mouth. “I can think of better things to put in your mouth, but this is the safest.”

Regina rolled her eyes, grabbed the mouthguard, and slowly slipped into her mouth as Emma watched with intense interest.

Three hours later, the two women were slowly moving into Regina’s apartment. The roller derby boot camp while being fun was also slightly dangerous. Emma had her arm around Regina’s shoulder, helping her in the apartment. She winced, looking at Regina’s bandaged wrist. Regina was a born natural roller derby queen, so much so that she became a Head Jammer. As a Jammer, Regina was well on her way to winning their practice game until an opposing Jammer rammed into her with a power jam. Regina took the jammer down with her in a chokehold and ended up falling fairly hard on her wrist. Thankfully, after a visit to an ER, it was only a slight sprain.

“Emma, I’m fine. I don’t need…assistance,” Regina said even though she was enjoying the nearness of the blonde, and she put emphasis on ‘ass’ because Emma’s other hand was close to her ass, and that’s all she could think about.

“I like giving you…assistance,” Emma batted her eyelashes at Regina and let her hand move closer to a destination that needed no assistance. “Plus, I feel like super guilty, and I’m hoping to alleviate some of the pain.” She then lowered her hand and gave a firm squeeze to Regina’s ass.

The ass squeeze got a wide-eyed response from Regina; then her eyes grew dark, lusty, and half-lidded as she gazed at Emma and leaned in closer.

Before Regina could try and kiss Emma, she noticed her kitchen light was on, and there was noise coming from that area. Emma watched Regina’s line of sight, and her eyebrows furrowed. Regina walked slowly to the kitchen, and Emma crept alongside her, ready to pounce in case the brunette was jumped again for the second time tonight. Okay, so Emma felt guilty that Regina got hurt, although Regina stated over and over again that she loved being introduced to roller derby boot camp. Plus, Regina loved the nickname Rejammer. When the noise got louder, they both charged into the kitchen to find a swearing redhead.

“Bloody hell!” Zelena yelled as she tried to open a wine bottle with a big knife.

“Zelena, what are you doing here?” Regina demanded, she wanted to add that she changed her locks so her sister couldn’t barge in anymore, but obviously, Zelena had figured that out.

“Oohhh, I like this,” Zelena’s eyes darted back and forth between Regina and Emma. “You two workout at the gym together, then come here to a more private workout?” She raised her eyebrows up and down in a suggestive manner.

“Your sister is not subtle,” Emma whispered in Regina’s ear.

Regina was about to answer when Zelena butted in once again.

“Darling, sister! What happened?” Zelena abandoned the bottle of wine she was trying to pry open with a knife and walked over to examine Regina’s bandaged wrist. “You have to be careful with restraints when playing.” Zelena winked to Emma.

“Your sister is a real badass roller derby jammer,” Emma adoringly smiled while staring at Regina in awe.

“Not surprisingly, there’s nothing my baby sister can’t do,” Zelena said with a warm smile directed at her sister. “Don’t think I’ve been prouder of Regina.” Zelena paused for a moment and hugged her sister, her eyes got watery as tears formed. “Please, tell me she broke some woman’s nose or tore someone’s piercings out.”

Regina shook her head and snorted; she couldn’t help smile; of course, this would be the thing her big sister would be proud of. Not all the money she makes for their family while ensuring their family legacy with new partnerships, no roller derby jammer, was more impressive to her sister.

Emma watched as Regina found the wine opener and effortlessly opened the bottle for Zelena. While Zelena was busy looking for cheese and crackers in Regina’s pantry, Regina walked close to Emma so she could whisper and not be heard by her sister.

“Can you stay? Until my sister leaves?” Regina asked with big eyes directed at Emma.

“Yeah, sure,” Emma smiled, oh if Regina used that look often, she was going to be pretty helpless in agreeing to anything the brunette requested of her. She was glad Regina asked her to stay because she surprised herself in not wanting to leave. Emma couldn’t help the dopey grin that spread across her face.

After two hours and two bottles of wine later, all three women were sprawled out on Regina’s living room couches. Emma wondered if Zelena was ever going to leave, it was getting quite late. Regina had refrained from drinking wine because of her injury. Emma felt a bit buzzed because Zelena kept refilling her glass. The blonde had a feeling there was an ulterior motive for all the drinking.

“Well, I think it’s time we all went to bed right, ladies?” Zelena stood up a bit wobbly and stretched.

Emma’s eyes went wide; yup there it is, she thought, the ulterior motive had appeared. Regina looked a bit taken back as well.

“Zelena, would you please get me some more water and ibuprofen from the kitchen?” Regina used the big eyes now on her sister, and it worked as Zelena huffed and puffed her way to the kitchen.

Regina used this opportunity to whisper urgently to Emma, “Don’t take this the wrong way, but can you…spend the whole night?” She tried her big eyes again on Emma.

“You want me to spend the night with you?” Emma’s grin grew wider, okay it might have been the wine, but also the thought of sleeping in the same bed with Regina was also a really good buzz.

Regina scrunched up her nose, “Looks like my sister is staying over. I don’t want to give her the wrong impression…”

“That we’re courting 18th-century style? Which is turning out to be surprisingly super hot to me,” Emma reached over and took hold of Regina’s non-bandaged hand.

“I’ll owe you,” Regina licked her lips as she stared into Emma’s eyes then lowered her gaze to her mouth.

“I’m sleeping in your bed tonight?” Emma tilted her head in a cocky gesture. “With you?”

Regina rolled her eyes with a mischievous glint in her eyes, “Yes.”

“Oh, I think that is payment enough,” Emma stared back at Regina’s lips.

Regina’s face became pink as she felt heat flood through her body, thinking of Emma in her bed.

Zelena swept back into the room gracefully yet also loud at the same time. She invaded Regina’s space by thrusting a refilled glass of water at her then holding out one pill.

“Here you go roller derby queen, take some ibuprofen in case it swells, and if there is any pain,” Zelena handed over a pill and motioned to the glass of water that Regina was holding.

Regina took the pill, swallowed it, and took a sip of water. Then suddenly, Zelena gasped and blurted out an ‘Oops!’

“Not what you want to hear after taking a pill from your shady sister,” Emma looked between Regina and Zelena.

“Hey, I sent you finger dick pics.” Zelena pointed and glared at Emma. “You’re welcome.”

“Zelena, you did what?” Regina turned to her sister with wide eyes. She was going to kill Zelena later; right now, she turned to stare back at Emma with a questioning look.

“She sent me photos of your hands,” Emma looked away sheepish because she enjoyed the photos too much.

Regina shook her head; she was going to kill Emma later too. She had another issue to worry about it. 

“Zelena, what drug did you give me?” Regina gritted her teeth and shot her sister a death glare.

“Hey! I don’t nilly willy drug, my baby sister!” Zelena crossed her arms against her chest in a power defense move. Then she deflated a bit. “Either Viagra or Ambien or maybe a Molly?” She shrugged her shoulders.

Emma gritted her teeth and winced while squinting her eyes at Zelena. “What does Viagra do to a woman?” Emma was kind of curious to find out the effects of the sexual enhancing drug on Regina, and then she scolded herself for thinking of that scenario.

Zelena reached over and rubbed Regina’s back. “Sorry, sis. And if it’s a Molly, we will be here for you and your journey.”

Regina stood up from the couch, seething at her sister. She grabbed Emma’s hand and began dragging her to the bedroom.

Emma was a bit stunned but also couldn’t help the smile tugging at her lips of this ridiculous situation and had no idea what kind of night she and Regina were going to have.

“Yes, you two go off and have a very goooood night.” Zelena yelled after them. “I’ve got noise-canceling headphones that I have no intention of using.”

As soon as Regina pulled Emma into her bedroom and closed the door, her mouth was on the blonde’s mouth.

Emma was stunned for a moment then melted into the kiss. This was the longest she had ever waited to kiss someone she was dating and damn if it wasn’t worth the wait because her toes were curling at finally having Regina’s lips. Emma felt her knees weaken; she reached out and wrapped her arms around Regina’s neck to pull her closer. Regina slid her tongue into Emma’s mouth, and she let out a loud moan. The kiss deepened further then for some reason, Regina began to fill heavy in her arms.

“It’s Ambien!” Zelena yelled from the living room as Regina fell limp in Emma’s arms.

Emma looked a little crestfallen then tried to mask her face. “You probably need rest after your injury.” She wiped the hair from Regina’s face as she gathered the woman up in her arms and carried her over to the king-sized bed.

She then went about removing Regina’s pants and decided to leave the tank top alone, which left both them in undies and tank tops as she lifted the covers to get the brunette all snuggled in. And make sure the injured wrist had its own pillow. Emma went around to the other side of the bed and crawled in; she had to suppress a giggle as she turned the lights off and whispered good night to Regina. This evening had not gone as she hoped; however, she did end up in Regina’s bed so she couldn’t stop the dopey grin across her face. She took a deep breath; she did the math in her head on the dates. They had been on four dates, with one date a week, and it had been about a month. Regina was almost the longest romantic relationship she had ever in her life, which she knew was a terrible fact. Usually, at this point in dating someone, a month felt like years but not with Regina. And she never had sleepovers with someone; that was a sure-fire way for someone to get too attached. Yet here Emma was sleeping over at Regina’s because she wanted her car back so much. Yup, she nodded to herself, that was the only reason she was breaking her own rule of sleeping over. She fell into a comfortable sleep next to Regina, listening to her breathing was more soothing than the sleepcasts she had been playing at night on her phone.

When morning light started to stream into Regina’s bedroom, the brunette didn’t mind as much as on other mornings because she felt really comfortable, and her body felt all tingly except her wrist, which was a little achy. She froze when the pillow she was hugging and laying on top of moved. Her brain slowly started functioning, and she realized she was on top of Emma, which felt like an almost naked Emma. And she also realized she was mostly naked as well.

“Where are our pants?” Regina managed to croak out through her grogginess. Regina lifted her head from Emma’s shoulder but didn’t bother moving or letting go of the blonde. Everything felt too good.

“On your floor. They were uncomfortable, and doesn’t this feel better,” Emma ran her bare, smooth leg against Regina’s naked thigh.

Emma had to admit she slept better last night than she had in a long time, and she didn’t feel the usual dread she felt when spending too much time with someone. The usual dread she felt, like a heavy anchor or a rusty hook, wasn’t sitting on top of her chest. This morning, her chest was light and airy.

“Stop that.” Regina scolded Emma but didn’t move away and truthfully did not want Emma to stop rubbing up against her legs, the bare skin felt heavenly. “I don’t remember much from last night.” She was a little worried what her sisterly drug-induced state let loose, at that thought Regina leaned up on her elbow.

“That’s because you’re sister put you to sleep, but not before you landed quite the kiss on me,” Emma lifted and tilted her head so she could see Regina’s stunned face.

Regina cleared her throat and disengaged herself partly from Emma’s body so she could sit up. “I kissed you under the influence of my sister’s sleeping curse?”

“It was a pretty grand goodnight kiss,” Emma grinned and sat up, getting closer to Regina. “Whether it was Ambien induced or not.”

“Are you saying you want a good morning kiss as well?” Regina arched her eyebrows at Emma.

“Seems like a good bookend for the date,” Emma arched her eyebrows in return. Yes, she wanted another kiss. Last night’s kiss had been nothing like she experienced before, and she was surprised she slept at all afterward, except that she had Regina close to her.

Regina didn’t think it was a good idea to start something now, so she changed the subject. It wasn’t a good idea to start kissing Emma half-dressed. “We didn’t even get cleaned up after the boot camp last night.”

The blonde was so close her body was aching to become in full contact with her again. Regina was shocked that they both had fallen asleep in their partial workout gear, and yet Emma smelled delicious this morning that she wanted to take a bite out of the blonde. That set off an alarming thought in her brain, how could Emma smell this good after working out and all night. She remembered an article she read about smells and partners; this did not bold well for her winning this bet. Damn her nose and hormones and Emma’s pheromones. This was only date four and she was beginning to wonder if she could dump Emma and her sweet-smelling pheromones; she feared what six more dates would do. Hopefully, Emma would do something absolutely disgusting and morally reprehensible so she could later cut ties and win her sister’s stupid bet. And more importantly, start smelling bad. She really would be doing the company and all the employees a massive favor if she could just shag Emma and move on. Yet she wondered if that was a favor to her heart.

Emma put her hands on Regina’s bare thighs. “How do you smell so amazing after that workout last night?” She wanted to lean over and bury her nose in Regina’s neck or even her armpit. She wrapped one arm around Regina’s waist and pulled the brunette almost entirely onto her lap.

Regina’s eyes went wide, and she ran her hands along Emma’s body up and around her neck, before she had a chance to ask Emma what she meant or kiss her senseless her bedroom door flew open and Zelena waltzed in holding a tray.

“Breakfast in bed for the happy couple,” Zelena came into the bedroom and sat on the bed next to Regina, who was almost in Emma’s lap now.

“Zelena get out!” Regina disengaged from Emma, got up on her knees and pointed towards the door. “Now!” She realized she was too horny, and that seemed to make her even angrier with her intruding sister.

“I brought sustenance to recharge from rigorous morning sex. Regina, you can mount the blonde stallion and take a nosh at the same time,” Zelena waved her hand over the food tray.

Regina and Emma both glared at Zelena then looked down at the tray of ‘sustenance’, which included a box of uncooked pasta, an apple, and half a loaf of grain wheat bread in the packaging. No beverages. 

Emma thought back to why Regina had asked her out on ten dates in the first place; it had to do with Zelena. She needed to ask Regina again what the bet was about because so far, she could see how Zelena was possibly the most annoying sister. She wanted to throw the redhead out of the room immediately. Emma was just about to forcibly remove Zelena from Regina’s bedroom until her phone started ringing. She fumbled out of bed, tangled in sheets and Regina’s legs. Regina and Zelena watched in amusement as Emma fell onto the floor then bounced back up trying to act cool. She really hope neither women noticed her underwear.

“She’s not graceful is she,” Zelena tilted her head as she watched Emma rummage through her bag for the ringing phone. Her eyes trailed the blonde’s toned legs. “She makes up for it in muscle, though.”

A growl came from Regina as she stood up and grabbed Zelean’s arm, she pulled and pushed until her sister was out of the room; she then locked the door. She turned to Emma, who was talking on the phone, giving out commands while struggling to put back on her stylish sweatpants. The commands were quite forceful, and Regina found herself getting even more turned on by the verbal demands than the half bare toned legs in front of her. Emma finished the call and looked up sheepishly to Regina.

“Do you have a shirt I can borrow?” Emma motioned down to her tank top.

“I don’t have enough time to go home before getting to work.”

Regina smirked as her eyes trailed down Emma’s body, “No pants?” She hadn’t missed the cartoon underwear Emma was wearing. “Some age-appropriate underwear, perhaps?”

“What you don’t like the Spongebob undies?” Emma looked down at her very colorful underwear. 

Okay, so sometimes Emma indulged her inner child who never got to have cartoon underwear as a kid. Emma never thought she would end up pantless with Regina last night, so that’s why she wore Spongebob instead of something else, perhaps sexier. Plus, wearing the pineapple house dweller panties meant that she would take things slow with Regina and not let her hormones run wild, as they tended to. She patted herself on the back for lasting to date four on intense handholding and what was fast becoming passionate eye sex with Regina.

Regina shook her head; she couldn’t believe she was dating someone who wore cartoon underwear. And she really couldn’t believe she wanted to pull off that ridiculous cartoon underwear with her teeth. She shook her head again; maybe the Ambien was letting her judgment become impaired.

“I think I can pull off the sweat pants if I have a nice shirt…oooh maybe one of your lady boss blazers?” Emma gave a puppy dog look to Regina. Emma used her charm on Regina for a shirt; it wasn’t lost on her how domestic this morning had been. In some ways, Emma had intensely craved and feared domesticity with someone for so very long. She paused when she realized and wished she didn’t have to rush off to work, usually something she did love rushing off to. Emma wanted to stay here in Regina’s bedroom even if all they did was more handholding and hopefully more kissing.

While she was lost in thought, Regina returned with a blouse from her closet. “Here’s one of my shirts…” Regina leaned into Emma and purred, “…if you return it in one piece…” Regain ghosted her lips over Emma’s lips, teasing a kiss, “…you’ll get a lot more.”

Emma grinned and decided to push her luck, “Like that black blazer?”

Regina rolled her eyes, “Fine. You can borrow the blazer.” She turned to make the bed while Emma grabbed the blazer she spotted in the closet last night while looking for Regina’s bathroom and dressed in a rush.

When Regina finished making the bed, Emma turned around looking quite stylish in last night’s track paints with a strip down the legs, her own elegant blouse, and she admitted the blazer set it off. Emma had put her hair up in a loose bun and gathered up all her stuff. Then she stopped to ask if she could borrow some of Regina’s products to finish cleaning up for work.

After Emma finished commandeering Regina’s bathroom and borrowing anything in her reach, Regina followed Emma out of the bedroom to say goodbye. Regina scowled when she saw Zelena in the kitchen sitting on a stool, drinking coffee and eating her food.

“Ooh, can I get some coffee?” Emma asked in a hurry as she turned to Regina.

“Coffee,” Regina spun around and pointed to her automatic coffee maker already had the magical brew waiting.

Regina pulled out a coffee mug and started filling it for Emma.

“Do you have another travel coffee thing?” Emma asked with a hopeful expression and smiled towards Regina.

“Honestly, Ms. Swan, you’re wearing my clothes, used all my toiletries, stole my toothbrush, and commandeered my make-up this morning…AND you want coffee to go?” The vein on Regina’s forehead began to bulge out.

“With a little creamer, 2% if you have it and with a sprinkle of cinnamon,” Emma gave a cheeky smile to Regina.

Regina glared at Emma.

“So married,” Zelena tilted her head and smirked.

Regina glared more harshly at Zelena. “Why aren’t you getting ready for work?” She filled a travel mug with 2% milk and a sprinkle of cinnamon and walked out of the kitchen with Emma following behind her.

Emma also gave a glare to Zelena, solidarity at all. She felt weird because she already wanted to see Regina later today to return her things and well to see her. She shook her head because that was seeing the same person twice in one day, very unusual for her. Emma felt her smile fade. She usually got excited if someone started to seem distant, almost made breaking up with them easier. She wasn’t ready to dump Regina yet, and she wondered if she would be in another two months or so, she sort of enjoyed the woman’s company.

The travel coffee mug was handed over to Emma as Regina let a smile spread across her face. Emma leaned in and brushed her lips against Regina’s cheek. She couldn’t stop herself from lingering and then pressing lips softly with a small kiss. Emma let the kiss linger a bit longer and inhaled deeply, trying to imprint Regina’s scent into her brain.

“Thanks again for the shirt and jacket,” Emma leaned in slowly and kissed Regina’s cheek again, her lips lingered, and she inhaled her scent. “Is this the part where I tell you to have a good day?”

“Yes,” Regina reached and fixed the slightly skewed blouse under her blazer that looked too damn good on the blonde. She really wanted to kiss Emma again and remember it but knew she had to leave so instead she just smiled. “I’ll call you later to make sure my clothes are still stain free.”

Emma gave Regina a smirk before leaving. They were both going to be very late for important work meetings.

When Emma caught her breath in the elevator, all she could do was think about the kiss from last night and the chaste cheek kiss from this morning, both different and both panties dropping.

Regina hurried around her apartment, rushing to get ready for work as well, and all she could think about was kissing Emma again and being Ambien and Zelena free to enjoy it.


	6. Dates 5-8

**DATE 5  
[The date montage continues]**

Both Regina and Emma decided on something simple for Date 5 since Regina’s wrist was still recovering from Date 4’s roller derby boot camp, so that is how they ended up at a local movie theater catching a new theatrical release. Emma sat happily with a giant tub of popcorn in her lap, and Regina had her Milk Duds. They exchanged snacks back and forth and shared a giant trough sized soda. They pressed their arms together on the armrest and held hands after the snacks were gone. Emma found it hard to concentrate on the movie with Regina’s warm, soft thumb rubbing circles on her palm, even with loud car chases and superheroes running around onscreen. Regina said she was picking the next movie and for Emma to be prepared because it would feature no action sequences or cartoons.

After the movie, Emma walked Regina back to her apartment, and she kissed Emma’s cheek and then trailed her lips down to the blonde’s neck. She placed an open mouth wet kiss on Emma’s pulse point. In some ways, Regina was enjoying torturing the blonde because from what she gathered, Emma was a bit of player, so taking things slow was fun to watch yet also insanely frustrating for her libido. Regina was in some ways glad her sister had interrupted her and Emma’s morning after because as slow as things were going, it was still a little fast for her despite her raging lady boner for the blonde.

Emma very reluctantly pulled away from Regina and nearly fell backward down the stoop steps with a goofy grin on her face. Regina’s kisses were more intoxicating than a case of beer. As much as she didn’t want to pull away, she thought waiting a bit longer was a good idea, plus Regina hadn’t invited her inside. She would go home and take matters into her own hands, thinking of Regina’s kisses.

**DATE 6  
[The date montage continues]**

Regina played up her wrist injury a little more to get a rowboat ride through Central Park by Emma. They rented a rowboat, and Emma rowed them around the scenic lake. Emma almost laughed out loud to herself when she thought how beautiful and also disgustingly romantic this date outing had gotten. Emma couldn’t believe she was in a rowboat rowing Regina around like she was a queen, and she was enjoying it.

The brunette sat across from the blonde in the rowboat and watched as Emma powered the oars masterfully, her strong muscles finally put to good use. Well, Regina could think of several other things to put those muscles to use in private. She tried not to think of the other things surrounded by all kinds of people in the park.

There were snacks and wine, which made Emma very happy. She had hoped Regina would be swayed by her athletic arm display of rowing and drop everything and jump her in the rowboat where they could commence hardcore lovemaking before the whole park. That fever dream did not happen, however when they went to part ways, Regina leaned over placed a chaste kiss on Emma’s lips.

**DATE 7**

Regina had actually approved mini-golf, Emma was confident the brunette would veto the activity. Emma drove the pair out to Jersey with her to play mini-golf. Emma told Regina it would be fun and good exercise, however, Regina knew it was secretly so the blonde could show off techniques for the kiddie sport and eat junk food. Emma’s techniques included standing behind Regina, pressing her full body against her under the guise of showing her a good golf swing. Regina didn’t mind Emma’s instructions at all, except that she was getting a tad overheated for a family activity with many kids running around.

The date ended with Emma dropping Regina off and getting a slightly less chaste kiss in the car. Emma knew all that golf demonstrating was going to pay off.

**[The date montage ends]**

**DATE 8**

Trying a new restaurant had been the plan for Date 8; however, both women deeming they had a rough, long week opted to stay in at Emma’s apartment and relax. The relaxing part then became working from home as both women were on their laptops, typing away in sweatpants and glasses. Regina had not arrived in sweatpants, but Emma insisted on the brunette getting comfy while they worked, so Emma loaned Regina some sweatpants and a well-worn t-shirt. Regina once again found herself getting lost in the scent of Emma on the clothes.

Hanging out in Emma’s apartment while both working in Emma’s clothes was not lost on both women once again how domesticated their evening had turned out. Generally, if something like this would ever to happen, it would ruffle Emma’s proverbial swan feathers, and she would dash out, yet with Regina, it felt strangely comforting.

They sat side by side on the couch, typing furiously away on their laptops, Regina more or less beating her keyboard as if it was a whack mole game. Snacks and beverages were all strewn across Emma’s coffee table.

“We can’t make out until I clear out my inbox for the day,” Emma broke the comfortable silence; she didn’t turn her head to look at Regina. She pretended to stare at her computer screen seriously, yet she wanted to gaze at the brunette next to her. Emma wanted to openly lust glare at Regain because she was wearing her glasses.

Regina rolled her eyes at the blonde, who was doing a terrible job of pretending not to stare at her.

“I didn’t say I was going to make out with you after this. Don’t flatter yourself.” 

Regina couldn’t help the smile that tugged on her lips because the possibility of kissing Emma or having some sort of physical contact was the main reason she conceded in coming to the blonde’s apartment instead of staying at her office. And she wanted to see what Emma’s apartment looked like; it was big loft in Brooklyn that was stylish, messy and very Emma like with a hasty made bed, some clothes thrown over a chair, a few exercise machines in one corner and an impressive kitchen for someone who claims they don’t cook. Emma’s bed did look cozy with several blankets and pillows tossed around; Regina wished they could just take a nap. Emma’s couch was comfortable too, a large L sized monstrosity that also felt cozy and nap appropriate.

“You came over here just to work?” Emma turned to Regina sad puppy dog eyes and the beginnings of a pout.

“You said we could both work tonight since we’re both behind and…” Regina stared into Emma’s eyes, momentarily getting lost, “…you said you would rather work together than not hang out for another week.” Regina was distracted with Emma in her glasses and touched by the blonde’s words. Her attraction to Emma was becoming almost unbearable, and the glasses might be the tipping point.

Emma pursed her lips in a goofy way; she had said that and she was pretty shocked; those words came out of her mouth, and she meant them. Even though prolonging another date for another week was good for her bet, she didn’t want to go another week without seeing Regina.

“You wanna know which cartoon underwear I’m wearing today.” Emma suggestively raised her eyebrows to Regina.

“I’m going to buy you age-appropriate underwear.” Regina turned back to her laptop but continued to watch Emma out of the corner of her eye.

“Oooh, I like the sound of that.” Emma really did like the sound of Regina buying her underwear, although she suspected that the brunette liked her silly undergarments as well. “And I’ll take that as a yes.” Emma pulled down her sweatpants just a little to reveal her brightly colored underwear.

As hard as she tried, Regina could not keep her eyes from straying from her laptop down to Emma’s fingers, where they were slowly pulling down her sweatpants to reveal some colorful cartoon character. Working was hard enough after a long, stressful week, and now sitting next to Emma showing off a sneak peek of her juvenile underwear, it was impossible to concentrate on anything besides kissing the silly blonde senseless.

“I have to answer these emails,” Regina turned back to her laptop. She was a little afraid to start kissing Emma; she knew if she did, she wouldn’t stop for the rest of the night and possibly for a long while.

“Talk about killing a mood,” Emma rolled her eyes at Regina then turned back to her laptop, “…okay…okay…I admit I need to do some work too.” She readjusted her glasses and started working and not thinking about Regina removing her animated undies.

Somewhere after the 100th email or so, Regina’s eyes become tired and very sleepy. She looked over to Emma who had already fallen asleep, with her laptop on her lap. Regina smiled as she gently closed her laptop, set it on the coffee table, and slid Emma’s computer from her grasp to set it aside as well. Regina was about to say she was going to leave when Emma reached up pulled her down to lay beside her on the couch. Emma wrapped her arm around Regina’s waist. Regina was too tired to go home, and Emma felt so good against her body. She wanted to enjoy the feel of Emma more, but she fell asleep quickly wrapped up in strong, warm arms.

The next thing Regina knew, she felt Emma’s hand rubbing her back. It was so soothing, it was almost luring her back to sleep as a mermaid luring someone out to sea, yet her eyes adjusted, and she could tell it was morning. The sun brightened up Emma’s airy loft; the blinds didn’t block out much light. 

“Do you not have any blinds?” Regina squinted her eyes as she raised herself on her elbow to look down at a smirking Emma.

“It’s better than an alarm clock, right?” Emma decided to be bold and continued to rub Regina’s back. She let her hand wander lower and caressed Regina’s lower back.

Regina then looked down at her and Emma’s body, they were covered with a blanket, but she also felt the delicious feeling of bare skin against her legs.

“Where are my pants?” Regina stared at Emma.

“On the floor probably,” Emma moved her leg to rub against Regina’s leg.

“Why?”

“Maybe we had sex?” Emma shrugged in a joking tone, yes they would have both remembered if they had sex.

“No, sadly, you fell asleep on top of your keyboard instead of me.”

“Ouch. I was exhausted last night,” Emma yawned and stretched as much as she could with Regina, still half laying on her. She was still really tired; there was a new deal at work that was beyond exhausting.

Regina smiled down at Emma; she ran her hand through Emma’s wavy hair.

“Still, maybe we attempted to have sex, and it was so rigorous and mind-blowing we both fell asleep in the middle of it.” Emma trailed one of her hands down Regina’s side.

Emma’s hand made Regina shiver. “That’s not high praise for your skills Swanova.”

“Hey, you got that from Ruby. Don’t listen to her,” Emma grumbled as she ran her hand up and fingers over Regina’s arm with faint teasing touches.

Emma moved, so her leg was in between Regina’s legs, their lower halves almost touching, which elicited a moan and an ‘Emma’ from Regina.

“Is this okay?” Emma asked she leaned up to place a soft kiss on Regina’s neck.

Regina moaned, “Yes…yes, it’s okay, but I need to get to work…” she wondered if Emma could feel how wet her underwear was after sleeping with Emma’s arms around her and now the blonde’s lips on her neck. She tried for coherent, logical thinking, “…have an early meeting….mmmmm….hence the reason I came over to work while you were working.” She didn’t care about the meeting anymore; surely, she could miss one meeting.

“We still have our underwear on so we’re safe,” Emma smirked, “I can’t get you pregnant through underwear despite how powerful the Powerpuff Girls are.”

Regina pulled back the blanket to look at Emma’s underwear, “Powerpuff Girls. Where do you find these ridiculous undergarments?”

Regina stared into Emma’s eyes then her eyes dropped down to the blonde’s lips. Her phone, which she thought she set to vibrate, started ringing incessantly, so her eyes moved from Emma’s lips to the kiss blocking device.

“You’re not seriously going to answer that, are you?” Emma reached out to grab Regina’s phone, but the brunette moved her arm too quickly. Then another ringtone joined and created a competing duet of annoying sounds.

“Don’t answer that,” Regina now glared at Emma’s phone.

Emma growled from underneath Regina. “Please, don’t let me be this horny all day. It’s kinda uncomfortable.” She thrusted her lower half into Regina’s core, and both women gasped at the contact.

Regina snorted at Emma’s crude comment but couldn’t help but reciprocate the movement of her hips against Emma’s. She decided to tease the blonde some more, even though she was caving and seconds away from tearing off the ridiculous underwear. She grabbed her arm and positioned herself, so she was straddling Emma’s hips. “Do you realize we had four dates without any chaperones?”

Emma nodded below Regina and perched her hands on Regina’s hips as the brunette slowly rocked against her.

“I’ve been ignoring all of Zelena’s calls and messages.” Regina gave Emma a wicked smile.

“Same with Ruby,” Emma furrowed her brows and concentrated on the smooth skin below her hands.

“So we’ve had a two morning afters now with no night before…do you want to come over tonight to have a proper morning after?” Regina down her lips, almost touching Emma’s lips.

“Yes. I can’t stress yes more than enough.” Emma cringed and squeezed her eyes shut. “In many many many ways, gawd yes, however…” Emma stared up into Regina’s eyes “…I have to go to Alice’s birthday party.”

Regina tried to hide her disappointment. “Oh, okay.” She sat up more and started to disentangle from Emma’s body.

“Do you want to go with me?” Emma couldn’t believe how natural and fast that question came firing out of her mouth. She wasn’t known for bringing anyone she was dating to friend gatherings; it was easier that way when Emma didn’t click with someone if her friends weren’t following who she was dating on some social media app thing. As Emma looked at Regina, she did want Regina to go to the corny game night with her and as her date.

Regina’s phone started ringing again and texts and email alerts sounding off as well. She reluctantly leaned over and grabbed her phone off the coffee table. She squinted her eyes at the screen then got the meanest scowl on her face. “Shit!” She jumped off of Emma and the couch and looked around for her clothes.

“What’s wrong?” Emma sat up quickly, looking for a way to help Regina.

“Zelena, she’s at work causing problems. I have to go…” Regina surveyed her clothes, the ones she wore yesterday. “…not sure I can pull off sweatpants business chic like you did.” She smirked at Emma.

In a whirlwind of organized chaos, Emma loaned Regina a respectable blouse and helped her get cleaned up for work, then sending her off with her travel coffee mug with Emma’s signature morning brew. When Emma handed off the coffee, she leaned in and placed a long, lingering kiss on Regina’s lips.

“Now… I’ll be just as uncomfortable all day like you,” Regina stared in Emma’s eyes.

This time it was Emma’s turn to snort, “Have a good day at work.” She leaned in again to give one more kiss to Regina.

When Regina arrived at work, she went as fast as she could to their main conference room. She could only imagine the amount of mess that Zelena was creating with one of their top clients. She strode into the conference room, and before she could address anyone, Zelena started talking.

“My sister is late for a meeting? I am at a meeting before my sister? Have I slipped into the upside-down world?” Zelena made a wide dramatic gesture holding her head.

Regina rolled her eyes, but she also couldn’t contain a small smirk as she sat down next to Zelena.

Zelena noticed her sister’s hair wasn’t completely perfect, and her clothes were slightly disheveled; in fact, Regina was wearing a shirt that wasn’t hers, and it was wrinkled. She knew this because at one point she had stolen quite a lot of sister’s shirts. A wrinkled blouse was nearly unheard of from her pristine immaculately coiffed baby sister Regina. She leaned over to whisper in Regina’s ear. 

“So looks like you didn’t wake up at home this morning. Finally.”

Regina felt her cheeks burn. How did Zelena always know, it was so infuriating. And in this case, it was true. She felt tingles and warmth shoot her body thinking of waking up in Emma’s arms. She would much rather be back on Emma’s couch tearing off her ludicrous underwear and feel those warm, soft hands on her thighs again.

Zelena leaned and got up in Regina’s personal space and stared way too close. 

“I don’t think you’ve shagged her yet. You spent the night over there but didn’t shag her? You didn’t shag her when I was there too.”

Everyone around the conference table looked at Regina then Zelena, everyone looked uncomfortable, and a few people snickered.

“Zelena, we’re in a meeting,” Regina gritted out, trying not to draw attention. “This is very inappropriate for work.” And all around inappropriate, Zelena made it sound like she almost shagged her girlfriend in front of her sister. Wait…did she just call Emma her girlfriend?

“Darling you are going to lose this bet and not even get laid. What am I going to do with you, baby sister?” Zelena tried to hug her sister, but Regina pushed her away.

There was an uncomfortable silence through the entire large conference room. Everyone made awkward eye contact with each other, not wanting to speak first regarding their boss’s sex or lack of sex life.

“Ms. Mills…uh…Ms. Mills….can we back to the discussion?” An older man sitting at a conference room table surrounded by a very stern, confused-looking group of serious business people stared at Regina and Zelena through the massive monitor screen mounted on the conference room wall.

Regina turned and saw that the conference room screen was live streaming with their client. She was furious with Zelena. She wanted to crawl underneath the table and hide, one of their top clients, and almost all their employees had just heard about her personal life. She was definitely going to sleep with Emma tonight to make sure her sister never ruined anything meeting ever again. And most importantly, because she was ready to be with Emma and she truly wanted to be with Emma despite the Zelena factor.

“Let me look that over again,” Regina pretended to be rereading as she frantically tried to figure out where they were in the meeting. All she could focus on was making Zelena suffer later and seeing Emma again.


	7. Date 9

It was unfortunate timing that Alice and Robyn’s monthly game night fell in between Regina and Emma’s date eight and ten. Emma tried as hard as she could to get out of it, but there was no way because this particular game night was also Alice’s birthday party. Ruby was insistent that Emma bring along Regina so everyone could meet her. Emma strongly disliked this idea. She had really hoped maybe Date 9 might be a naked date night. They had been dating now for two months and things were going well, definitely well enough Emma thought to get to the winning three-month mark. Yet she was a little worried now that sex would mess that up, so maybe having sex wasn’t a good idea, and the game night was better. Regina hadn’t been in a rush to have sex either, yet they both seemed to be wildly attracted to each other, that Emma knew for sure. They hadn’t even made out yet; she knew once she got to kiss Regina again thoroughly, Emma wasn’t letting go of her, and she was reasonably confident Regina felt the same way. It would be near impossible for them to put the brakes on if they started something. Still she was very anxious about taking the sex plunge, damn Ruby for getting in her head. She didn’t know if waiting on sex had enamored her more on Regina or if she had liked Regina for who she was without the sex clouding her mind, yet another reason to have sex, Emma thought. Sex might clear up her true feelings for Regina or show that she doesn’t have any.

As they walked closer to Emma’s friend’s apartment, Regina found herself getting more nervous. She wanted Emma’s friends to like her. Although, Regina had already kissed the birthday girl and dumped a cold beer in her other friend’s lap, so that was an icebreaker. She found herself getting attached to the blonde, she was really beginning to question if she could stop seeing Emma in only a week or two. Regina didn’t want to think this was Date 9, which meant technically they only had one date left. She might need to fudge the numbers a bit. So maybe her sister was right, and she couldn’t do casual dating, it bothered her that Zelena knew her so well. And she realized it might upset her more, not seeing Emma. She had some thinking to do later. She was surprised they hadn’t had sex yet. She had lied to Zelena the other day, they ended up not seeing each other that night because of work restrictions. Regina was so turned on after some of their dates she had taken matters into her own hands quite a few times. They had come close on a few dates and then Emma would slowly pull back. Regina wasn’t sure why Emma seemed almost to get scared when they got close to sex, as uncomfortable as that conversation might be, Regina knew she was going to ask the blonde.

“I’m going to apologize in advance for my friends,” Emma said, breaking Regina out of her thoughts. She motioned for Regina to take the stairs first into the building.

“Well, at least it’s not one of my sister’s rowdy dinner parties. I hope you don’t have to attend one of those,” Regina said over her shoulder to Emma behind her.

“I don’t mind,” Emma found herself replying quickly, surprised at herself for offering. She actually did want to see Regina’s annoying, obnoxious sister again if it meant more time with Regina.

As soon as they stepped inside Ruby and Dorothy’s apartment, Regina and Emma were surrounded by Alice, Robyn, Ruby and Dorothy all hugging and welcoming them to the game night birthday party.

Emma took a deep breath and started the introductions.

“That’s Alice. You remember her, right?” Emma pointed to Alice who blushed and Robyn squinted her eyes. She then pointed to Robyn standing next to Alice with her arm around her waist. “Robyn her not so better half because she was the one in the control box pointing us out to the kiss cam operator.” Emma glared at Robyn. “Three times. Really three times, Robyn?” She held up three fingers for emphasis and level of annoyance as she continued to glare at her.

Robyn just shrugged, “It’s uhhh…the comedy rule, right?” She gave Emma a sheepish look then ducked her head in Alice’s shoulder.

Regina nodded and smiled at both young women, “Nice to formally meet you both under better and more formal circumstances.”

“That’s Ruby and her better half, Dorothy,” Emma motioned to Ruby and Dorothy, who both smiled at Regina.

They moved into the living room where their other friends Mary Margret and her husband David, sat along with another friend Grumpy.

“Hey, Grumpy,” Emma walked over to the partly gray-bearded man and hugged him. “I thought you hated games?” She raised her eyebrows at Grumpy.

“You can’t believe everything I tweet,” Grumpy nodded to Regina as a welcome, then sat back down and started chugging his beer.

“Good to know,” Emma moved onto Mary Margret and David to introduce them to Regina. “This is Mary Margret and David, the old married couple of the group.”

Just as everyone was getting settled down to start playing games, there was a knock at the door.

Ruby went over to answer the door, and Regina froze when she heard the voice coming from the front.

“Seriously?” Regina pushed her drink into Emma’s hand and stood up just as Zelena strolled into the living room.

“Hello all, I’m Zelena, Regina’s dear sister,” Zelena made a wave to Regina, who scowled back at her in return. “Regina was kind of enough to extend the invitation; I hope it’s not a bother.”

“I did NOT extend.” Regina stomped up to her sister to grab her elbow and pull her back to the front door. “Yes, it’s a bother. Zelena, how did you find us?”

Zelena stood firm and gracefully pulled her arm from Regina’s stronghold. “Dear sister, you never turned off your location tracking on your phone.”

“I never turned it ON darling sister,” Regina growled slowly with a low deep, menacing voice.

Everyone in the room got quiet and watched the sisters with wide eyes, especially Grumpy, who looked like he was moments away from starting a chant of, ‘Fight! Fight! Fight!’ until Emma walked over and thumped him in the arm. Grumpy yelped in pain.

Ruby’s eyes darted back and forth between Regina and Zelena several times before she spoke. 

“Zelena, the invitation is extended if you would like to stay and play games with us, celebrating the birthday girl.” Ruby motioned to Alice who smiled big. Emma reached over smacked Ruby’s arm hard enough for her to yelp. Both Grumpy and Ruby were rubbing their arms in pain.

“Let’s get you a drink sister,” Grumpy stood up and led Zelena into the kitchen to get her a drink, he needed another beer anyway.

Emma pulled Regina aside and asked quietly. “Why is your sister here?”

Regina let out a deep sigh. “Remember that stupid bet I told you about?”

Emma grinned, “Yeah, kind of the reason we’re on ten dates.” Although, her grin faded when she saw Regina’s face became more serious. And she was going to have to come clean with her bet soon and find out if they had to stop at ten dates because the thought of there not being a Date 11 gave Emma a stomach ache.

“My sister is here because she doesn’t think we are actually dating. She didn’t think we had sex that night you stayed over,” Regina rolled her eyes.

“We didn’t have sex. Were we supposed to have sex? I thought sex was date ten? Or maybe later tonight.” Emma leaned in closer to Regina. “Besides just because we didn’t have sex doesn’t mean we’re not dating.”

Regina smiled at Emma. She felt torn, she wanted Zelena out of the company willingly with no drama, yet Emma was the first person she dated in a long while that made her feel like her stomach had been taken over with a flurry of love-struck butterflies.

The games started up, and Ruby started dividing up people for the Pictionary teams. She decided to separate the couples, so on one team was: Ruby, Regina, Robyn, David, and Grumpy. And the other team included Emma, Zelena, Alice, Mary Margret, and Dorothy. Ruby was the captain of the Wolf Team, while Emma was the captain of the Swan Team.

The board games commenced, and things got extremely competitive between the two sisters. When it came to Pictionary, both Zelena and Regina were yelling at their team members to draw better. Emma trying to be supportive started drawing worse in hopes Regina’s team would win, but then Zelena had swatted her hard, almost spanked her so she decided to draw as well as her terrible skills would allow her.

Ruby rolled the dice since it was their turn; the Wolf team landed on an ‘All Play’ square in the board, which meant the Swan team could draw at the same time to take the lead away from the Wolf Team. It was Regina’s turn to draw for the Wolf team and Zelena’s turn to draw for the Swan team. They each got their turn looking at the card, and they both scoffed. Emma took a deep breath looking back and forth between the dueling sisters.

“Bloody hell,” Zelena let slip out, indicting it was going to be a hard one to draw.

Regina shook her head and let out a long exasperated sigh after seeing the card. Emma watched both of the women closely. The two sisters went frantically to work, trying to illustrate the object on their card. There were lots of scribbling going on while their teams looked on with furrowed brows, utter confusion on all faces watching the two illustrators.

“The ground!” Emma yelled too fast while scrunching up her face trying to decipher Zelena’s drawing.

Zelena rolled her eyes at Emma and kept drawing.

“Uhh….a stage?” Mary Margret suggested.

Zelena huffed, and then pointed more at her drawing pad. She growled then drew some more nonsense.

“A bed!” Emma yelled out. Zelena yelled back, “Yes!” And gave the blonde a big smile and thumbs up. 

On the other side of the table, Regina scribbled away on her drawing board. She scowled that Zelena was slightly ahead of her.

“So we know it’s a bed,” Ruby said, and Regina lifted up her head to scowl at her. “What? Do you want to waste more time drawing…a bed?” Ruby pointed to the drawing pad, which clearly meant she didn’t think Regina, had been drawing a bed.

It was clear Regina’s drawing of a ‘bed’ was pretty horrible. Regina drew more and became a bit exasperated.

“A coffin!” Grumpy yelled.

“No, it’s a bed. We’ve already established that.” Ruby shot back quickly to Grumpy.

“So someone sleeping…and possibly having a seizure?” Robyn said and Regina nodded with a scrunched up a face and encouraged the young woman to keep going. “Dreaming!” Regina excitedly jumped up and down; she encouraged Robyn enthusiastically to keep going and guessing.  
Meanwhile, Zelena moved onto drawing something else, a big circle with some lines inside.

“Chakram! It’s a Chakram!” Emma yelled out with her hands over her head in excitement, confident that was the correct answer.

Zelena drew more to the circle, zig-zag lines through the middle, then squiggly lines at the bottom hanging off the circle.

Emma tilted her head in confusion; “It’s a Chakram with tendrils!”

Other team members looked perplexed at the drawing then at Emma.

“It’s a Chakram with braids! That’s it!” Emma jumped up and yelled. 

“Tentacles!”

“Warrior princess lay off!” Zelena yelled and glared at Emma.

“It’s her baby fish mouth,” Mary Margret said as she tried to get Emma to stop shouting ‘Chakram!’ again.

“That looks like a bunch of mixed-up lines,” Alice said in a low voice, but Zelena shot her a death glare for the drawing critique.

Zelena drew some more lines coming from what appeared from the stick figure on the so-called bed.

“Is that lightening? From their head?” Emma asked, she ran her hand over her face. She snuck a glance at Regina, who wasn’t fairing any better with her team.

“A wizard! It’s Harry Potter!” Alice screamed with joy.

Zelena shook her head and threw one of the markers at Alice.

Regina started drawing harder and making deep lines on the drawing pad; her team members winced at the aggression and anger she was giving out to that poor drawing pad. The brunette looked as if she wanted to set the drawing pad on fire.

“Can you draw something resembling anything?” Ruby shouted as the time started to run out.

Regina turned around and gave the coldest, scariest stares to Ruby. Ruby felt a shiver go down her spine.

On the other side, Zelena frantically drew and drew, more nonsense filling up her drawing pad as her team looked on defeat.

More suggestions started were yelled constantly as the time was running out to guess the right answer.

“Time!” Dorothy yelled out over everybody’s other yelling.

Both sisters threw their makers down in frustration and said in unison, “Dream catcher.”

Both teams still looked confused and perplexed. Emma tilted her head while mouthing the word ‘dream catcher’ to herself. A few others shrugged. Mary Margret tried for a good cheer of ‘We’ll get the next one team!’, which nobody believed.

“If you say baby fish mouth, I will punch you in the mouth.” Regina glared as Ruby was about to speak.

Ruby looked a little afraid of Regina, she jumped up and paused before saying it was time for a break to get more drinks and to prepare the birthday cake. Emma walked over to Regina with her hands tucked in pockets, and a sheepish smile on her face.

“Game night is fun, right?” Emma asked shyly to Regina.

Zelena strolled up to both of them; she draped one arm over each of Emma and Regina’s shoulders. 

“Take your little stud muffin and take a break. I do hope she’s wearing Spongebob underwear again.”

Everyone in the room stared at Emma, and their eyes lowered to below her waist.

“Actually, it’s…She-Ra today,” Emma’s cheeks turned pink as Regina pulled her along to the hallway.

“Where is the bathroom?” Regina asked, looking down the hallway.

Emma took over and pulled Regina along until they were standing in front of the bathroom. “There you go.” Emma waved her hand for Regina to go ahead. She expected Regina to enter and close the door; she didn’t expect Regina to pull her along with her in the bathroom and shut the door.

“You need to smudge my lipstick for this to be believable,” Regina ran her fingers through her hair roughly, really messing it up and unbuttoned buttons on her blouse, displaying lots of cleavage.

“What’s happening?” Emma couldn’t stop staring at Regina’s chest with even more of it on show. She was utterly awestruck by Regina’s boobs.

“I wanna get Zelena off my back, let’s pretend to…” Emma stared at Regina intensely, waiting for her to finish her sentence, “…have a quickie in the bathroom.” Regina said slowly and in a breathless low voice.

Emma’s eyes went wide with her face flushed pink, and her warms cheeks were nothing compared to the heat and electricity coiling up in her body at the thought of finally being with Regina in a naked way. Okay, naked in this small bathroom was not what she had in mind, but at least if she wanted to help Regina fulfill this request, she needed to take a more hands-on approach.

“Sure, I can get on board with that,” Emma reached up and pulled her sweater and shirt up and over her head, leaving her in her sports bra. She hoped Regina would take off her top too, although she didn’t want their first time to be in a bathroom with their family and friends a few feet away. However, she was so wet poor She-Ra was probably drowning by now.

“You didn’t have to take your shirt off …it’s uh…” Regina stumbled over her words, seeing Emma almost topless rendered her speechless, she licked her lips as her eyes roamed over Emma’s chest and torso. She really wanted Emma completely topless. “Just pretend.”

“Getting in the mood for the scene,” Emma knew that was a lie; she had been in the mood to ravage Regina since she saw her at the bar.

Regina reached up and lifted her finger to her lip and smeared her lipstick. She ran the same finger over Emma’s lips, smearing the color of lipstick over the blonde’s mouth.

“The best way to make it truly believable is to….” Emma trailed off softly as she stared longingly at Regina’s lips.

Regina leaned and was mere inches from Emma’s lips, “…well if it’s the best way…” she wanted to kiss Emma, she felt cheated that she didn’t remember their first kiss, no thanks to Zelena. She ached to remember that kiss.

“Here, give me a…hickey,” Regina opened her shirt all the way and gestured to her neck.

Emma’s breathing became ragged, and her eyebrows raised high as she stared hungrily at Regina.

“You want me to give a hickey?” Emma pulled back to look Regina in the eyes. She wondered if she heard the brunette right. “You want a hickey voluntarily?” Emma whispered out; she wanted to give hickeys all over Regina’s body.

“I don’t necessarily want a juvenile lust mark…but yes do it…please,” Regina pulled Emma closer to her and whispered in her ear.

With Regina’s body flush against Emma’s and the request lustily whispered was all Emma need to latch on her lips to Regina’s neck and started passionately kissing and sucking.

“You can suck harder…” Regina moaned as Emma kissed and sucked on her neck, the moaning wasn’t pretending at all. “…and bite if you want…” she was having a really hard time forming sentences as Emma’s mouth sucked harder, and she could feel her tongue slide against her skin.

After several minutes of Emma sucking so hard on Regina’s neck that she almost became an honorary vampire, Regina slowly pushed Emma away. They both had labored breathing.

“Here…give me one too,” Emma pulled Regina off the sink and leaned against the wall, her hands went to Regina’s waist and tugged her flush against her body.

“God yes…” Regina wanted nothing more than to have her lips on Emma “…I mean good idea.” Her libido was in overdrive.

“Regina…” Emma managed to choke out, the sensations of Regina sucking on her neck, and then surprisingly, the brunette’s hand went lower and cupped her ass.

The two women lost track of time; they also tuned out the noises and chatter of their friends and family in the next room. They could only hear each other’s breathing and longing.

Emma tangled her hands in Regina’s hair. She ran her hand over Regina’s cheek and pushed up her head and lowered her head so she could land her lips on Regina’s. Regina moaned as Emma’s mouth smashed against her mouth, heat flooded her body. Emma’s tongue slid into Regina’s mouth, and they both let out a moan.

Suddenly, a slight crash broke their sex haze, and they both looked to the door, both aware now where they were and how close they had come to crossing the line in a friend’s bathroom.

“Well that was embarrassing…I almost came with you just sucking on my neck.”

“Emma…do you want to leave and go back to my place?” asked Regina as she stared hard at Emma.

“Yes, please, yes,” Emma croaked out, her voice horse with hunger. “I’m too gay and horny to function right now…my underwear is toast.”

Emma and Regina tried to put back their clothes in the most presentable way possible before exiting the bathroom. Ruby startled them standing outside in the hallway, waiting for them.

“Did you just do it in my bathroom?”

“What?” Emma scoffed, okay yeah they came close but she had refrained, just barely.

“That’s kinda rude, Swan. Can’t believe you just fucked in my bathroom.”

“Our bathroom,” Dorothy interjected as she came walking down the hallway.

“You’re never getting that car back.” Ruby crossed her arms against her chest as she stared hard at Emma.

Zelena now walked to the overcrowded hallway.

“Ooh, she shagged you in the bathroom, didn’t think you had it in your sis, nice work.” Zelena gave an ‘Atta girl’ pat on the back to Emma.

“What if I shagged HER?” Regina turned to glare at her obnoxious sister.

“Please, Regina,” Zelena said in a condescending tone.

“You don’t think I can fuck someone in a bathroom,” Regina said this loudly with spite and anger directly at Zelena. “Because I can. I can FUCK someone anywhere. I’m not a prude.”

Zelena eyed her sister up and down, looking over Regina’s clothes and then landed on the massive hickey on her neck.

“You never learn, do you…Swanova,” Ruby laughed at Emma.

Emma ran her hands through her hair in frustration.

“Ruby, we didn’t do anything in the bathroom.” Emma blurted out without thinking. Emma really wanted to do something in the bathroom. “We haven’t had sex yet! There are you happy!” Emma knew as soon as those words left her mouth, they might help her, but they were going to damage Regina.

“I am happy! You’re finally maybe growing the fuck up, Swan!” Ruby yelled at Emma, and even though her words were supportive, she sounded slightly angry.

Dorothy watched Ruby closely. “Are you jealous? Do you still have a thing for Emma?” Asked Dorothy with a raised voice.

“No!” both Emma and Ruby said at the same time towards Dorothy.

“That kiss cam video was funny though,” Alice appeared in the way overcrowded hallway.

“What kiss?” Dorothy turned to glare at Ruby. “You kissed Emma?”

“No…well sort of…but not really…” Ruby tried to explain as Dorothy pushed her way through to get out of the hallway. “It was just a peck at the baseball game!”

“Eh, it was more than a peck,” Alice chimed in, then realizing her mistake when Robyn appeared and slapped her arm.

Dorothy headed towards their bedroom and slammed the door.

“Emma kissed me!” Ruby yelled through the closed door. “Dorothy! I only wanna win that car! That’s it, babe!”

Back in the overcrowded hallway, Zelena focused again on her sister.

“You haven’t shagged yet? At all?” Zelena looked between Regina and Emma.

Regina fumed and glared at Emma as the blonde turned with an apologetic look towards the brunette.

“Wait…what does she mean win?” Regina continued to glare at Emma, “What car?”

Emma looked like a deer caught in headlights.

“Regina darling, this is supposed to be a fling. Why are you meeting her posse?”

“Why are you here? You’re making it ten times worse. You’re my sister.” Regina shot back to Zelena.

Emma put her hand on Regina’s shoulder, and the brunette tensed up, which was not lost on Zelena. The two women stared intensely at each other, Emma never letting go of Regina. There was enough sexual tension between these two women to generate electricity for a small seaside town for 28 years, at least.

“It’s clear the two of you haven’t shagged yet.”

“Zelena, how can we when you keep showing up on our dates!”

“They haven’t?” asked Ruby as she walked back into the overcrowded hallway, followed by Grumpy. “Ha! Emma this is great! It’s progress.”

Zelena scoffed and put her hand up. “Excuse me, but I’m trying to get my sister laid here.”

“Excuse me, but I’m trying to get a wife for my friend.” Ruby shot back and glared at Zelena, then she added in a lower voice. “And win a car.”

Regina and Emma started at both with stunned faces.

“She’s trying to find you a wife?” Regina’s eyebrows went up high in surprise as she stared at Emma, then her brows furrowed. “Wait…are you dating me to win a car?”

Damnit, Ruby, Emma wanted to scream out loud to her friend. This was not how she wanted to tell Regina of the silly bet. She had thought maybe she would explain the situation to Regina, and then they would laugh it off while they drove around the city in her reacquired car.

“No. It just started that way. Sort of.” Words rushed out of Emma’s mouth, she was tired of not telling Regina, but this was the worst place to tell her. Regina pushed through the small group of people, putting distance between her Emma. Emma turned back to Ruby, furious, “I want my car back, Ruby! It’s mine!”

Regina stopped when she got back into the living room, the only two people not enjoying the drama were the married straight couple, David and Mary Margaret who looked at everything with wide eyes. The straight couple looked like they were trapped in their least favorite franchise of real housewives.

Everyone stayed quiet for a moment. Regina pursed her lips, ran her hand through her hair, and took a deep breath. She needed to think for a second. How was it possible she wondered that Emma also had a bet on their dates? Did their dates truly mean nothing to her? Anger started to boil up; she was furious with Emma.

“I’m counting that one time you brought me coffee as a date. You’re done, Emma. Ten dates completed.” Regina went to grab her coat and purse from the side chair. She wanted to leave immediately.

“Perfect, now you can dump her and move on,” Zelena said with a sneer and a little gleeful joy as she grabbed her coat and purse to follow her sister.

Emma felt like she had been punched in the gut, the wind knocked out of her. Was Regina dumping her now? That’s it, no more dates. Technically they had one more. If she could stretch until next week that was three months, Emma then scolded her stupid brain for thinking of the car again.

“This was all about you just getting laid?” Emma bolted in front of Regina, preventing her from leaving the apartment.

“Uh, darling…dumping,” Zelena had a wicked smile on her face. She did love messy drama.

“So ten dates was only ten dates. That’s it? You’re just going to dump me?” Emma felt like she was going to throw up.

Ruby walked back into the living room. “Emma kind of needs to be dumped I agree with that. She needs to be dumped more.”

“Stay out of it, Ruby,” Emma turned on her friend and glared at her.

“You’re just usually the dumper, you need to be the dumpee sometimes,” Ruby glared right back at Emma.

“Well, considered Emma dumped,” Zelena gently grabbed her sister’s arm to move them to the front door again. “Let’s go, Regina.”

Dorothy emerged from the master bedroom. “Ruby, you seem overly invested in Emma.” Ruby’s partner seemed particularly pissed off. Dorothy headed towards to exit the apartment as well.

Ruby watched open-mouthed as Dorothy stormed out of their home. 

“Dorothy! Where are you going? I’m happy for her! This is happy, not jelly!”

“Regina…” Emma reached out to touch Regina, and the brunette pulled away.

“You and me …we’re done,” Regina said in a cold tone as if finishing a business transaction. “Ten dates completed.”

“That means I win the car, Swan!” Ruby yelled out from the hallway.

Regina and Zelena walked past Emma and left the apartment.

“Shut up Ruby!” Emma felt like not only she got punched in the gut, but her chest ached too. “I don’t care about the car.” She mumbled softly, but it was too late for Regina to hear, she was gone. Emma didn’t get the car or the girl. She knew which one hurt worse.


	8. Date 10?

The elevator doors pinged, Zelena swished and sashed through her family company’s offices. Zelena was surprised Regina was back at work the next day and from office gossip, her sister was even earlier than usual. She had wanted to win this bet, but after seeing how crushed Regina looked last night, she wasn’t sure anymore. Admittedly, she had wanted a reason to quit the family business, it was dreadfully boring to her and the bet seemed a really fun way to exit. And in her own way, she had wanted to help her sister; she wanted her to have some fun and date someone that wasn’t incredibly dull. Someone possibly completely frivolous, and to prove to her sister sex didn’t mean you had to marry someone. 

Surprisingly, after watching Regina and Emma together, the blonde turned out to be a better match for her sister than anyone else she had ever seen her date. And she had begun to hope that maybe her sister was right and the silly blonde would lead to marriage. Yet, she also knew Regina and the company business was important than love or sex. Zelena had seen her sister sacrifice her happiness for the family more times than she cared to recall, she wanted her sister to start putting herself first, be selfish like she was.

Zelena walked into Regina’s office and saw her sister with her glasses on sitting at her desk reading over papers, her eyes look puffy and red. As always, Regina looked immaculate and the model lady CEO.

“Sis, are you okay?” Zelena put her purse down on a chair and walked to stand next to Regina seated at her desk.

“I’m fine,” Regina said in a soft voice, not looking up from her papers.

“Did your ten...” Zelena paused and smirked, “…your nine night stand follow you home last night?” Zelena studied her sister carefully. Regina looked tired, upset but also something else she couldn’t put her finger on.

Regina didn’t answer her sister, and before Zelena could make some sort of witty remark, she heard some commotion from the hallway. A few people had stood up from their cubicles to watch a flash of blonde and leather sprint through the offices yelling, ‘Regina!’

Emma stopped in front of Regina’s office, out of breath. Her eyes zeroed in when she saw Regina at her desk, she ran into the office.

“Don’t come any closer,” Regina looked up from her papers to glare at Emma.

“Regina…” Emma was breathless; she clung onto the brunette’s name as if it were a life preserver, and she was sinking. She inched closer to Regina’s desk.

“Emma…you have no idea who you’re dealing with,” Regina tilted her head and glared even harder at Emma.

“You just left? That’s it?’” Despite what Regina said, Emma continued to get closer to the brunette’s desk and the woman herself.

Regina looked very annoyed to see the blonde in her office.

“Did the two of you have another date after the party last night?” Zelena looked back and forth between the two tense women.

Emma glared at Zelena, “This doesn’t concern you, especially since you told Regina to dump me.”

Regina scoffed, “You were only dating me for a car. What difference does it make?”

“Oooh, I do hope it was at least a nice car,” Zelena crossed her arms against her chest as she leaned on Regina’s desk.

“Yeah, it’s a yellow Volkswagen Beetle,” Emma puffed out chest and stood tall in front of both sisters.

Both sisters scrunched up their faces and shook their heads at Emma.

“What? It’s the best car!” Emma yelled at both women. “Zelena can you please leave so I can talk to Regina in private.”

“No,” Regina said to Emma with a hard stare. “Anything you have to say to me, you can say in front of my sister.”

Emma’s shoulder slumped in a defeated gesture.

“Okay, yes…it started because of a stupid bet…” Emma moved closer to Regina, who stayed planted firmly behind her desk as a buffer. “But that’s the thing. You weren’t only a bet. Things changed…we had something Regina…we had moments…” Emma felt herself holding her breath, she didn’t know what to say.

Zelena continued to watch both women, she wished she had popcorn.

Regina took off her glasses, stood up and looked up at Emma. “Emma, we have nothing in common. We’re too different. The only thing we have in common was…” she trailed off and Zelena watched her sister closely. 

Regina leaned slightly over the desk to stare into Emma’s eyes. “It was fun, but it’s over. And I’ve got work to do.” Regina motioned to the small mountain of papers on her desk.

Emma stared at Regina, tears welled up in her eyes. “Bullshit. I know you, Regina, you like me. You felt something.” She glanced at Zelena then mouthed to Regina, ‘Last night.’ She hoped Zelena didn’t catch the reference.

Regina felt her face flush. She also felt anger course through her veins, specifically the vein in her forehead that popped out now. “I’m sorry if I gave you the wrong impression. Sorry, if my lunatic sister gave you the wrong impression.” Regina straightened her back and took a deep breath as she stared hard at Emma. “And quite frankly, I’m not going to settle down with someone who has yellow hair. It’s ridiculous as you are.”

Emma winced, ouch that one hurt, she thought, and her hair wasn’t yellow necessarily.

“Now, Miss Swan…do I need to call security or can you please leave my office and…my life peacefully?” Regina said firmly, even though her hands were shaking.

Not only was Zelena frozen listening to her sister dump someone ruthlessly, so was the whole office as everyone was dead silent like in a horror movie before the last time the killer pops up again.

Emma dropped her head, sniffed, and ran her hand across her nose. She didn’t look at Regina again as she got the hell out of Regina’s office as fast as she could.

Regina sat back down in her chair, put her glasses back on, and started reading over her papers again as if nothing had happened.

“Regina…I think she did like you,” Zelena didn’t even care about the silly bet anymore, she wanted to make sure Regina knew what she was doing.

“I won. I went on ten dates. We had sex.” Regina looked up to stare at Zelena on the verge of tears.

“You did.”

Zelena can see the hurt and sadness in Regina’s eyes. She continued to stare at what appeared to be her heartbroken sister. She walked out of Regina’s office. She felt something must have happened after game night last night because Regina seemed different. Even the way Regina and Emma looked at each other had been changed this morning. She thought something did happen, so her sister had finally sealed the sexual deal with the blonde. Regina was a closer, and she would ultimately do whatever it took, within moral and legal means, to close a deal. She knew Regina wanted her gone from the company. She didn’t realize she was willing to risk her happiness to achieve that goal.

Zelena smoothed her hands down over her dress and walked out to the bigger office area where all the cubicles were, she pulled a chair out and motioned to two people to hold her hand while she used the chair to stand on one of the desks. There always had to be a dramatic flair with Zelena.

Regina stood up and walked out of her office to watch her sister. She had hoped this day would come, just never estimated the mixed emotions it would bring.

“Hello, everyone. I have an announcement to make…due to other exciting opportunities…” Zelena kept building up the dramatic effect “…I will be leaving the company…” before Zelena could finish her statement, there are a few ‘Yays,’ and ‘Woohoos’ heard murmured throughout the office floor. “Rude.” Zelena frowned as she motioned for the two people to come back over so she could get down off the desk, but they walked away.

Regina couldn’t help a smirk tugging at her lips; then, it faded away when Zelena turned her head to smile at her. She walked over and held the chair and reached out her hand so Zelena could step down to the floor.

“Shall I escort you out of the building? Or would you prefer security to have the honor?” Regina asked Zelena with raised eyebrows.

“No offense, dear sister, but I think for the dramatic departure, security would be better. Make sure you ask for Hank and tell him that he will be carrying me out bridal style.” Zelena ran her hands through her hair to get ready for her grand goodbye.

Regina pinched the bride of her nose, walked back to her desk, and called up the building security to escort Zelena out of the company.

*****

After the excitement died down after Zelena’s announcement, Regina told her assistant she would be taking a few days off. She needed some peace and quiet out of the city, to decompress after the last few months and a certain blonde. As Regina drove out of the city, she felt the stress slowly fall away from her body. Having Zelena leave the company was going to make work a hell of lot easier. She had decided to spend a few days in a remote cabin near some great hiking trails and a gorgeous lake. She wanted the seclusion and privacy. When she got out of the car, she took a deep breath and smiled, she brought her bags inside the cabin and started to get her belongings settled.

Suddenly, the door of the cabin flew open, startling Regina. She turned around quickly.

There stood Emma staring back at Regina with wide eyes and breathing hard. Regina looked back at Emma with wide eyes.

“You had to insult my hair?” Emma tilted her head as she gazed at Regina.

“I had to make it look real. And you’re fine,” Regina smirked at Emma. She did notice the blonde’s hair was very stylized, not as many curls. “What did you do to your hair?”

“I got a blowout, had to convince Ruby I was going out to ya know…,” Emma ran her fingers through her hair, she noticed that Regina watched her every move; they were definitely going to have some fun in this cabin. 

She couldn’t wait to get closer to Regina.

“So, do you think she bought it?” Regina moved closer to Emma. She couldn’t wait to touch her again. Regina wanted to run her hands all over Emma’s body like she had last night. And get her hands tangled in that yellow hair she loved so much.

“Yeah, I think she did. I don’t know your sister very well, but she looked pretty stunned when you dumped me.”

“You were very convincing,” Regina reached out and ran her fingers down Emma’s cheek. She cupped her cheek. Regina knew she had been harsh with Emma; it was the only way Zelena would buy it. And Emma had said the night before anything she could do to help Regina, she would do. As long as they could keep seeing each other, still, Regina fake dumping Emma had been one of the hardest things she had to do in life. Her heart clenched and ached at the thought of not seeing Emma again.

“Nice work, brutal yet very convincing…maybe a little too convincing,” Emma reached out and put her hand on Regina’s waist. She pulled Regina flush up against her body.

Regina shook her head. “I didn’t like doing that; it gave me a raging headache.” Emma reached up with one hand and gently massaged Regina’s scalp. “Now …let’s really win this bet. Last night was pretty…” before Regina would finish her sentence, Emma jumped in.

“Fucking fantastic,” Emma placed a hot, wet open mouth kiss along Regina’s jawline.

“Short…” Regina tugged on Emma and pushed her towards the bedroom in the cabin. “Oh yes…” Regina moaned when Emma sucked on her neck, “…it was fucking fantastic.”

Emma kissed up Regina’s neck, then across her cheek to the corner of her mouth, then fully on her lips. Both women grabbed a tight hold of each other and surged forward, kissing each other with the pent up passion of eight dates of chaste hand-holding.

Regina pulled Emma along to the bedroom as they continued to kiss and gasped when Emma tore her bloused down the middle with buttons flying down to the worn hardwood floors. Emma gasped when Regina pushed her down on the bed and ripped her tight jeans away. During the night, they managed to knock over a lamp, shattering it to pieces and destroy the antique bed frame. As the sun started to rise and orgasms slowed down, Regina and Emma collapsed in each other’s arms exhausted on a blissful sex high.

The next afternoon when they finally awoke from a sex haze, they hit the shower and made a mental note to leave extra money aside to pay for the repairs due to the shower fixtures and glass door getting broken during rigorous showering. Regina and Emma had no idea that the flimsy glass shower door was so unstable and were shocked when they never fell over onto the floor, thankfully Emma held on to Regina’s torso as her hands were buried in the woman’s lower region.

After a few rounds in the bed and shower, they were both hungry, so they went to the kitchen where they didn’t get very far without tearing a cabinet door off while Emma lifted Regina to wrap her legs around her waist.

When they finally decided to try and leave the cabin to check out the hiking trails, Regina was shocked to discover about herself that she could be persuaded to have sex in the woods. Up against a tree twice and once near a lake.

*****

After their blissful week sequestered away in the remote cabin where all they did was eat, sleep, hike, and have sex on every piece of surface, Regina and Emma knew they had to go back to work. They wanted to stay in their sex bubble, yet work was piling up for both of them. They drove back to the city in the car Regina rented, listening to music and handing holds. At one point, they had to turn off the road when Regina’s hands wandered, and Emma couldn’t concentrate on driving at all. It was a good road trip, with both women arriving in the city tired and sated. They decided to spend the night at Regina’s apartment, after spending nearly a week sleeping together, spending the night apart didn’t seem possible. As they walked up Regina’s street near her building, they held hands with a backpack slung over their shoulders. They were too preoccupied with each other to notice two people sitting on the steps to Regina’s building.

A slow clap between the two people on the steps finally broke Regina and Emma’s gaze from each other eyes.

Zelena and Ruby were sitting and staring at Regina and Emma as they approached the steps.

Regina and Emma stopped in their tracks with wide eyes; they turned to each other with raised eyebrows as well.

“What are you two doing here?” asked Regina; she still held Emma’s hand.

“What are you two doing?” Zelena smirked, “Besides each other.” She tilted her head in a cocky knowing way.

Ruby stood up and jumped down off the steps as she stared at Emma, “Heads up, Swan.” Emma raised her hand just in time to catch the keys that Ruby tossed to her. “You win.”

“And you lose…dear sister,” Zelena had the biggest grin on her face as she stood up and walked closer to Regina.

Regina squinted her eyes at Zelena.

“Hope you haven’t redecorated my office yet,” Zelena smiled at Regina.

Regina felt her stomach drop out; she knew it had to be too good to be true. She realized she could handle Zelena being at work if it meant Emma was still in her life. The thought of not being with Emma was worse than working with Zelena. She felt Emma’s comforting hand on her lower back; the blonde then leaned over and kissed Regina’s cheek.

“No, not yet…can we expect you back tomorrow morning?” Regina tried to sound sincere, but she knew dread was creeping into her voice.

Zelena made her sister wait for an entirely too long uncomfortable silence before she spoke.

“I’m going to have to turn you down. I have other exciting opportunities to pursue,” Zelena smiled warmly at her sister. “I’m glad you finally got a good shag, it was beginning to look a little hopeless.”

Regina let go of Emma’s hand and moved to hug her sister. “Thank you, Zelena.” She whispered in Zelena’s ear. She was more thankful for the push towards Emma than leaving the company, although that was a wonderful silver lining.

Zelena pulled back to stare at her sister. “Even your skin looks clearer now after that long dry spell.”

Regina swatted her sister and moved back to Emma’s side and wrapped her arm around the blonde’s waist. All Emma could do was stare into Regina’s eyes with a love-struck dopey look on her face.

“Monogamy looks good on your Swan,” Ruby said while watching Emma and Regina swoon over each other.

Regina and Emma walked past Zelena and Ruby, up the stairs to the entrance to the building.

Ruby moved to stand next to the redhead. “Zelena?”

“Yes, Ruby, my darling wonderful new friend,” Zelena turned to smile at Ruby.

Ruby nodded towards Regina and Emma as they opened the door to the building.

“I think they’re get married in the next six months,” Ruby glanced back over to Regina and Emma, who briefly turned around, rolled their eyes in unison, and then shook their heads.

“No way, long engagement.” Zelena crossed her arms against her chest as she watched the happy couple trying to get away from them.

“Wanna bet on it?” Ruby grinned at Zelena.

Regina and Emma slammed the door to the apartment building, locking out Zelena and Ruby from entering the building.

“Of course,” Zelena reached and shook Ruby’s hand.

**Works inspired by this one:**

  * [Ten Night Stand [Art]](https://archiveofourown.org/works/20433410) by [hollysparrilla](https://archiveofourown.org/users/hollysparrilla/pseuds/hollysparrilla)


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